Cumulative Subject and Author Indexes, and Tables of Contents for Volumes 1-53

Advances in Carbohydrate Chemistry and Biochemistry

Volume 54

Cumulative Subject and Contributor Indexes and Tables of Contents

Volumes 1-53

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Advances in Carbohydrate Chemistry

and Biochemistry

Editor

DEREK HORTON The American University

Washington, DC

Board of Advisors LAURENS ANDERSON DAVtD R. BUNDLE STEPHEN J. ANGYAL STEPHEN HANESSIAN HANS H. BAER BENGT LINDBERG CLINTON E. BALLOU HANS PAULSEN JOHN S. BRIMACOMBE NATHAN SHARON J. GRANT BUCHANAN J. F. G. VLIEGENTHART

ROY L. WHISTLER

Volume 54

Cumulative Subject and Contributor Indexes and Tables of Contents

Volumes 1-53

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CONTENTS

PREFACE .............. vii

CONTENTS OF VOLUMES 1-53 .... ix

SUBJECT INDEX ........... 1

CONTRIBUTOR INDEX ..... .533

V

PREFACE

This 54th volume of Advances in Carbohydrate Chemistry and Biochemistry is an index volume that covers all previous volumes in the series, with a cumulative subject index of the content of all published chapters, along with an index of authors contributing the chapters.

The series began with the 1945 appearance of Volume 1 of Advances in Car- bohydrate Chemistry under the editorship of Ward Pigman and Melville Wol- from, and was the first serial publication of a new company named Academic Press, founded by Kurt Jacoby. The stated policy was to have the individual contributors furnish critical, integrating reviews rather than mere literature sur- veys, and to have the articles presented in such a form as to be intelligible to the average chemist rather than only to the specialist. The series was to cover the broad field of carbohydrates, including sugars, polysaccharides, and glycosides, and to include biochemical, industrial, and analytical developments.

The founding policy has been sustained throughout the subsequent evolution of the series, under the editorship of Wolfrom for most of the volumes until his death in 1969, of R. Stuart Tipson from 1954 until 1990, and of the present editor since 1969. The essential component of biochemical aspects was emphasized when the title was changed, in 1969, to Advances in Carbohydrate Chemistry and Biochemistry. The field of carbohydrates has undergone enormous expansion during the half-century that Advances has been in existence, and the pages of the past 53 volumes have recorded important developments in practically all aspects of carbohydrate science. Some of the articles have constituted status re- ports on areas still under active expansion, while others record definitive information of permanent reference value.

To enhance the utility of Advances as a reference source, the provision of good indexes has been an important objective, and each volume has contained a comprehensive name index of all authors cited in the individual chapters, along with a detailed subject index. Responsibility for compiling the subject indexes from the outset and for more than four decades was largely entrusted to a leading expert on indexing and nomenclature, Dr. Leonard T. Capell of Chemical Ab- stracts Service. These subject indexes were integrated into cumulative indexes of principal topics and have appeared in selected issues, with volume 29 containing

PREFACE ...

Vlll

such an index for volumes 1-29, while those appearing in volumes 35, 40, 45, and 50 refer in each case to the preceding five volumes.

The present index volume largely follows the model used successfully for the Methods in Enzymology series published by Academic Press, and the cumulative subject index has been compiled directly from subject indexes in the individual volumes. It is recognized that a lack of total uniformity is inevitable as a conse- quence of unevenness in some of the indexes, and most importantly, from the progress that has been made toward uniformity in carbohydrate nomenclature. Current nomenclature recommendations are recorded in the 1996 document Nomenclature of Carbohydrates, issued by the International Union of Pure and Applied Chemistry and the International Union of Biochemistry and Molecular Biology, which has been published in Volume 52 of Advances in Carbohydrate Chemistry and Biochemistry.

This index volume is complemented by a cumulative contributor index, and it is hoped that the volume will facilitate the retrieval of information and signifi- cantly enhance the utility of the entire series.

Washington, DC June 1999

DEREK HORTON

CONTENTS OF VOLUMES 1-53

VOLUME 1

The Fischer Cyanohydrin Synthesis and the Configurations ofHigher-Carbon Sugars and Alcohols ........................................... C. S. HUDSON

1

The Altrose Group of Substances . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37 NELSON K. RICHTMYER

CarbohydrateOrthoesters ..................................................... 77 EUGENE PACSU

Thio-and Seleno-sugars ....................................................... 129 ALBERT L. RAYMOND

The Carbohydrate Components of the Cardiac Glycosides . . . . . . . . . . . . . . . . . . . . . . . . . . 147 ROBERT c. ELDERFIELD

Metabolism of the Sugar Alcohols and Their Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . 175 C. JELLEFF CARR AND JOHN C. KRANTZ, JK.

The Chemistry of the Nucleic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 193 R. STUART TIPSON

TheFractionationofStarch .................................................... 247 THOMAS JOHN SCHOCH

Preparation and Properties of Starch Esters . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 279 ROY L. WHISTLER

Cellulose Esters of Organic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 309 CHARLES R. FORDYCE

A Discussion of Methods of Value in Research on Plant Polyuronides . . . . . . . . . . . . . . . . . 329 ERNEST ANDERSON AND LILA SANDS

VOLUME 2

Melezitose and Turanose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . C. S. HUDSON

1

ix

X CONTENTS OF VOLUMES 1-53

The Chemistry of Anhydro Sugars .............................................. 37 STANLEY PEAT

AnalogsofAscorbic Acid ...................................................... 79 F. SMITH

Synthesis of Hexitols and Pentitols from Unsaturated Polyhydric Alcohols ............. 107 R. LESPLEAU

The Interrelation of Carbohydrate and Fat Metabolism ............................. 119 HARRY J. DEUEL, JR., AND MARGARET G. MOREHOUSE

The Chemistry of Mucopolysaccharides and Mucoproteins .......................... 161 M. STACEY

Bacterial Polysaccharides ...................................................... 203 TAYLOR H. EVANS AND HAROLD HIBBERT

The Chemistry of Pectic Materials ............................................... 235 E. L. HIRST AND J. K. N. JONES

The Polyfructosans and Difructose Anhydrides .................................... 253 EMMA J . MCDONALD

Cellulose Ethers of Industrial Significance ........................................ 279 JOSEPH F. HASKINS

VOLUME 3

Historical Aspects of Emil Fischers Fundamental Conventions for Writing Stereo-Formulas in a Plane ............................................. 1 C. S. HUDSON

The Structure and Reactivity of the Hydrazone

E. G. V. PERCIVAL and Osazone Derivatives of the Sugars ........................................... 23

The Chemistry and Configuration of the Cyclitols .................................. 45 HEWITT G. FLETCHER, JR.

TritylEthersofCarbobydrates ................................................. 79 BURCKHARDT HELFERICH

Glutose and the Unfermentable Reducing Substances in Cane Molasses ............... 113 LOUIS SATTLER

The Halogen Oxidation of Simple Carbohydrates, Excluding the Action of Periodic Acid ............................................ 129 JOHN W. GREEN

CONTENTS OF VOLUMES 1-53 xi

The Molecular Constitution of Cellulose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 185 JACK COMPTON

Isotopic Tracers in the Study of Carbohydrate Metabolism . . . . . . . . . . . . . . . . . . . . . . . . . . 229 SAMUEL GURM

Products of the Enzymic Degradation of Starch and Glycogen . . . . . . . . . . . . . . . . . . . . . . . 253 KARL MYREIACK

The Polysaccharides of Mycobacterium Tuberculosis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31 1 M. STACEY AND P. W. KENT

The Chemistry of Streptomycin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 337 R. U. LEMIEUX AND M. L. WOLFROM

VOLUME 4

The Structure and Configuration of Sucrose (a-D-~~ucopyranosy~-~-D-fructofuranoside) ....................................... 1 IRVING LEVI AND CLIFFORD B. Pmvts

Blood Group Polysaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37 H. G. BRAY AND M. STACEY

Apiose and the Glycosides of the Parsley Plant. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . C. S. HUDSON

57

Biochemical Reductions a t the Expense of Sugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . CARL NEUBERG

75

The Acylated Nitriles of Aldonic Acids and Their Degradation . . . . . . . . . . . . . . . . . . . . . . . 119 VENANCIO DEULOFEU

Wood Saccbarification ......................................................... 154 ELWIN E. HARRIS

The Use of Boric Acid for the Determination of the Configuration of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 189 J. BOESEKEN

The Hexitols and Some of Their Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 211 ROLLAND LOHMAR AND R. M. GOEPP. JR.

Plant Gums and Mucilages . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 243 J. K. N. JONES AND F. SMITH

The Utilization of Sucrose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 293 L. F. WIGGMS

xii CONTENTS OF VOLUMES 1-53

VOLUME 5

Applications in the Carbohydrate Field of Reductive Desulfurization by Raney Nickel . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . HEWIT? G. FLETCHER, JR., AND NELSON K. RICHTMYER

1

Enzymatic Synthesis of Sucrose and Other Disaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . W. Z. HASSID AND M. DOUDOROFF

29

Principles Underlying Enzyme Specificity in the Domain of Carbohydrates . . . . . . . . . . . . 49 ALFRED GOITSCHALK

Enzymes Acting on Pectic Substances . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Z. I. KERTESZ AND R. J. MCCOLLOCH

79

The Relative Crystallinity of Celluloses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 103 R. F. NICKERSON

The Commercial Production of Crystalline Dextrose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127 G. R. DEAN AND J. B. GOTTFRIED

The Methyl Ethers of D-GlUCOSe . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 145 E. J. BOURNE AND STANLEY PEAT

Anhydrides of the Pentitols and Hexitols.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 191 L. F. WIGGINS

Action of Certain Alpha Amylases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 229 MARY L. CALDWELL AND MILDRED ADAMS

Xylan .............. ... .. .. .. ... ..... ......... ... .......... .... ...... ... ..... 269 ROY L. WHISTLER

VOLUME 6

Obituary of Walter Norman Haworth . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . E. L. HIRST

The Methyl Ethers of he galactose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . D. J. BELL

Thesynthesis ofOligosaccbarides ............................................... W. L. EVANS, D. D. REYNOLDS, AND E. A. TALLEY

The Formation of Furan Compounds from Hexoses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . F. H. NEWTH

Cuprammonium-Glycoside Complexes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . RICHARD E. REEVES

1

11

27

83

107

... CONTENTS OF VOLUMES 1-53 xi11

TheChemistryofRibose ....................................................... 135 ROGER W. JEANLOZ AND HEWITT G. FI.ETCIIER. JR.

The 2-(Aldo-polydroxyalkyl)benzimidazoles . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 195 NELSON K. RICHTMYER

Trends in the Development of Granular Adsorbents for Sugar Refining . . . . . . . . . . . . . . . 205 ELLIOTT P. BARRETT

Acoritic Acid, a By-product in the Manufacture of Sugar.. . . . . . . . . . . . . . . . . . . . . . . . . . . 231 ROBERT ELLSWORTH MILLER AND SIDNEY M. CANTOR

Friedel-Crafts and Grignard Processes in the Carbohydrate Series . . . . . . . . . . . . . . . . . . . 251 WILLIAM A. BONNER

The Nitromethane and 2-Nitroethanol Syntheses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 291 JOHN C. SOWDEN

VOLUME 7

The Methyl Ethers of the Aldopentoses and of Rhamnose and Fucose . . . . . . . . . . . . . . . . . R. A. LAIDLAW AND (THE LATE) E. G. V. PERCIVAL

1,6-Anhydrohexofuranoses, a New Class of Hexosans . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . R. J. DIMLER

Fructose and Its Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . C. P. BARRY AND JOHN HONEYMAN

Psicose, Sorbose, and Tagatose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . J. V. KARABINOS

1

37

53

99

Acetals and Ketals of the Tetritols, Pentitols, and Hexitols . . . . . . . . . . . . . . . . . . . . . . . . . . . 137 S. A. BARKER AND E. J. BOURNE

TheGlycals .................................................................. 209 BURCKHARDT HELFERICH

The Chemistry of the 2-Amino Sugars (2-Amino-2-deoxy-sugars) . . . . . . . . . . . . . . . . . . . . . 247 A. B. FOSTER AND M. STACEY

The Size and Shape of Some Polysaccharide Molecules.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 289 C. T. GREENWOOD

VOLUME 8

Relative Reactivities of Hydroxyl Groups of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . JAMES M. SUGIHARA

1

xiv CONTENTS OF VOLUMES 1-53

The Chemistry of the 2-Desoxysugars ............................................ 45 W. G. OVEREND AND M. STACEY

Sulfonic Esters of Carbohydrates ................................................ 107 R. STUART TIPSON

The Methyl Ethers of o-Mannose ................................................ 217 G. 0. ASPINALL

The Chemical Synthesis of o-Glucuronic Acid ..................................... 231 C. L. MEHLTRETTER

o-Glucuronic Acid in Metabolism ............................................... 251 H. G. BRAY

The Substituted-Sucrose Structure of Melezitose ................................... 277 EDWARD J. HEHRE

Composition of Cane Juice and Cane Final Molasses ............................... 291 W. W. BINKLEY AND M. L. WOLFROM

SeaweedPolysaccharides ....................................................... 315 T. MOM

VOLUME 9

Some Implications in Carbohydrate Chemistry of Theories Relating to the Mechanisms of Replacement Reactions ..................................... 1 R. U. LEMIEUX

Alkali-Sensitive Glycosides ..................................................... 59 CLINTON E. BALLOU

The 2-Hydroxyglycals ......................................................... 97 MARY GRACE BLAIR

The Methyl Ethers of Hexuronic Acids ........................................... 131 G. 0. ASPINALL

The Raffinose Family of Oligosaccharides ........................................ 149 DEXTER FRENCH

The Conjugates of o-Glucuronic Acid of Animal Origin ............................. 185 ROBERT S. TEAGUE

Color and Turbidity of Sugar Products ........................................... 247 R. W. LIGGETT AND VICTOR R. DEITZ

CONTENTS OF VOLUMES 1-53 XV

Carboxymethylcellulose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 28.5 J. V. KARABINOS AND MARJORIE H m m u

Paper Chromatography of Carbohydrates and Related Compounds . . . . . . . . . . . . . . . . . . 304 GEORGE N. KOWKABANY

VOLUME 10

The Stereochemistry of Cyclic Derivatives of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . J. A. MILLS

1

Column Chromatography of Sugars and Their Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . W. W. B~NKLEV

55

Glycosylamines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . G. P. ELLIS AND JOHN HONEYMAN

95

The Amadori Rearrangement ................................................... 169 JOHN E. HODGE

The Glycosyl Halides and Their Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 207 L. J. HAYNES AND F. H. NEWTH

The Methyl Ethers of the Aldopentoses and of Rhamnose and Fucose . . . . . . . . . . . . . . . . . 257 GEORGE G. MAHER

The Methyl Ethers of D-Galactose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 273 GEORGE G. MAHER

Polysaccharides Associated with Wood Cellulose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 283 W. J. POLGLASE

Thechemistry ofHeparin ..................................................... 335 A. B. FOSTER A N D A. J. HUGGARD

VOLUME 11

Periodate Oxidation of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ' M. BOBBITT

1

TheOsones . .. ..... ... ...... .. . . .. . .. .. .. . ..... . .. .. .. ... ........ .... .. . .. ... S. BAYNE AND J. A. FEWSTER

43

Reactions of Monosaccharides with P-Ketonic Esters and Related Substances . . . . . . . . . . 97 F. GARCIA CONZALEZ

xvi CONTENTS OF VOLUMES 1-53

Kojic Acid ................................................................... 145 ANDREW BEELIK

The Biosynthesis of the Monosaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 185 L. HOUGH AND J. K. N. JONES

Branched-Chain Sugars of Natural Occurrence . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 263 F. SHAFIZADEH

Nucleic Acids ................................................................ 285 G. R. BARKER

Aspects of the Physical Chemistry of Starch . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 335 C. T. GREENWOOD

Addendum .................................................................. 385 The Size and Shape of Some Polysaccharide Molecules

VOLUME 12

InfraredSpectraofCarbohydrates .............................................. 13 W. BROCK NEELY

The Saccharinic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35 JOHN C. SOWDEN

Zone Electrophoresis of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . A. B. FOSTER

85

SugarNitrates ................................................................ 117 JOHN HONEYMAN AND J. W. W. MORGAN

BenzylEthers ofsugars ........................................................ 137 CHESTER M. MCCLOSKEY

Methyl and Phenyl Glycosides of the Common Sugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 158 J. CONCHIE, G. A. LEVVY, AND c . A. MARSH

The Schardinger Dextrins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 189 DEXTER FRENCH

The Molecular Structure of Glycogens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 261 D. J. MANNERS

The Biosynthesis of Hyaluronic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 299 ROY L. WHISTLER AND E. J. OLSON

CONTENTS OF VOLUMES 1-53 xvii

VOLUME 13

Formation and Cleavage of the Oxygen Ring in Sugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . F. SHAFIZADEH

9

The Lobry De Bruyn-Alberda Van Ekenstein Transformation . . . . . . . . . . . . . . . . . . . . . . . JOHN C. SPECK, JR.

63

The Formazan Reaction in Carbohydrate Research . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105 L. MESTER

The Four-Carbon Saccharinic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 169 JAMES D. CRUM

The Methyl Ethers of 2-Amino-2-deoxy Sugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 189 ROGER W. JEANLOZ

Glycosyl Ureides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 215 IRVING GOODMAN

The Nonulosaminic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 237 F. ZILLIKEN AND M. W. WHITEHOUSE

Neuraminic Acids and Related Compounds (Sialic Acids) . . . . . . . . . . . . . . . . . . . . . . . . . . . 237 F. ZILLIKEN AND M. W. WHITEHOUSF

Polysaccharide Hydrocolloids of Commerce . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 265 LEONARD STOLOFF

Alkaline Degradation of Polysaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 289 ROY L. WHISTLER AND J. N. BEMILLFR

Starch Nitrate ................................................................ 331 GEORGE V. CAESAR

VOLUME 14

Action of Lead Tetraacetate on the Sugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . A. S. PERLIN

9

TheMaillard Reaction. ........................................................ 63 G. P. ELLIS

TheCyclitols ................................................................. 135 s. J. ANGYAL AND LAURENS ANDERSON

Aspects of the Chemistry of the Amino Sugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 213 A. B. FOSTER AND D. HORTON

xviii CONTENTS OF VOLUMES 1-53

PyrimidineNucleosides ........................................................ 283 J. J. FOX AND I. WEWEN

Preparation and Properties of P-Glucuronidase . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 381 G. A. LEVVY AND C. A. MARSH

Structural Chemistry of the Hemicelluloses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 429 G. 0. ASPINALL

VOLUME 15

Constitution and Physicochemical Properties of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . B. CAPON AND W. G. OVEREND

11

Methods in Structural Polysaccharide Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . HANS 0. BOWENF AND BENFT LINDBERC

53

The Carbonates and Thiocarbonates of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . L. HOUGH, J. E. PRIDDLE. AND R. S. THEOBALD

91

Tables of Properties of 2-Amino-2-deoxy Sugars and Their Derivatives . . . . . . . . . . . . . . . . 159 D. HORTON

Bacterial Nucleosides and Nucleotides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 201 J. JONSEN AND S . LALAND

The Biosynthesis of Aromatic Compounds from o-Glucose . . . . . . . . . . . . . . . . . . . . . . . . . . 235 DAVID B. SPRINSON

Polysaccharides of Gram-Negative Bacteria . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 271 D. A. L. DAVIES

Dextran: Structure and Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 341 W. BROCK NEELY

Chitin. ...................................................................... 371 A. B. FOSTER AND J. M. WEBBER

VOLUME 16

Radiation Chemistry of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . GLYN 0. PHILLIPS

.... 13

Applications of Trifluoroacetic Anhydride in Carbohydratechemistry ...................................................... 59 T. G. BONNER

CONTENTS OF VOLUMES 1-53 XIX

Glycosyl Fluorides and Azides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 85 FRITZ MICHEEL AND ALMLITH k E M t K

The Dialdehydes from the Periudate Oxidation of Carbohydrates . . . . . . . . . . . . . . . . . . . 105 R. D. GUTHRIE

Lactose ..................................................................... 159 JOHN R. CLAMP, L. HOUGH, JOHN L. HICKSON, AND ROY L. WHISTLER

Glycolipids of Acid-Fast Bacteria . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 207 EDGAR LEDERER

Galactosidases ............................................................... 239 KURT WALLENFELS AND OM PRAKASti MALHOTRA

The Fractionation of Starch . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 299 J. MUETGEERT

Carbohydrates in the Soil . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . , 335 N. C. MEHTA, P. DUBACH, AND H. D w t i

VOLUME 17

Higher-Carbon Sugars ........................................................ 15 J. M. WEBBER

The Sugars of the Cardiac Glycosides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . T. REICHSTEIN AND EKKEHARC WEKS

65

Oligosaccharides ............................................................. 121 R. W. BAILEY AND J. B. PIUDHAM

Selective Catalytic Oxidation of Carbohydrates, Employing Platinum Catalysts . . . . . . . . . 169 K. HEWS AND H. PAULSEN

Dicarhonyl Carbohydrates ..................................................... 223 OLOF THEANDER

PurineNucleosides ............................................................ 301 JOHN A. MONTGOMERY AND H. JEANETTE THOMAS

Enzymic Synthesis and Degradation of Starch and Glycogen . . . . . . . . . . . . . . . . . . . . . . . . . 371 D. J. MANNERS

VOLUME 18

Photochemistry of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . GLYN 0. PHILLIPS

. . . . I 9

xx CONTENTS OF VOLUMES 1-53

Paper Electrophoresis of Carbohydrates .......................................... 61 H. WEIGEL

Chemistry of Osotriazoles ...................................................... 99 HASSAN EL KHADEM

Developments in the Chemistry of Thio Sugars .................................... 123 D. HORTON AND D. H. HUTSON

Trehaloses ................................................................... 201 GORDON G. BIRCH

Naturally Occurring C-Glycosyl Compounds ...................................... 227 L. J. HAYNES

Chemistry of the Amino Sugars Derived from Antibiotic Substances .................. 259 JAMES D. DUTCHER

Biosynthesis of Saccharides from Glycopyranosyl Esters of Nucleotides (Sugar Nucleotides) ....................................... 309 ELIZABETH F. NEUFELD AND W. Z. HASSID

Physical Properties of Solutions of Polysaccharides ................................. 357 W. BANKS AND C. T. GREENWOOD

VOLUME 19

Crystal-Structure Analysis in Carbohydrate Chemistry ............................. G. A. JEFFREY AND R. D. ROSENSTEIN

7

Infrared Spectroscopy and Carbohydrate Chemistry ............................... 23 H. SPEDDINC

NuclearMagneticResouance ................................................... 51 L. D. HALL

Gas-Liquid Chromatography of Carbohydrate Derivatives .......................... 95 C. T. BISHOP

The Action of Hydrogen Peroxide on Carbohydrates and Related Compounds .......... 149 G. J. MOODY

3-Deoxyglycosuloses (3-Deoxyglycosones) and

E. F. L. J. ANET the Degradation ofcarbohydrates ............................................... 181

Structure and Some Reactions of Cellulose ........................................ 219 DAVID M. JONES

CONTENTS OF VOLUMES 1b.53 xx1

Wood Hemicelluloses: Part I . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 247 T. E. TIMELL

The Pneumococcal Polysaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 303 M. J. HOW, J. S. BRIMACOMBE, AN11 M. STACEY

VOLUME 20

Chemical and Physical Studies of Cyclitols Containing Four or Five Hydroxyl Groups .................................................. G. E. MCCASLAND

11

Unsaturated Sugars ........................................................... 67 R. J. FERRIER

ChemistryofOsazones ........................................................ 139 HASSAN EL KHADEM

Sulfates of the Simple Sugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 183 J. R. TURVEY

Cyclic Acetals of the Aldoses and Aldosides . . , . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 219 A. N. DE BELDER

Reactions of Amino Sugars with P-Dicarhonyl Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . 303 F. GARCiA GONZALEZ AND A. GOMIZ SANCHEZ

Naturally Occurring C-Glycosyl Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 357 L. J. HAYNES

Phenol-Carbohydrate Derivatives in Higher Plants . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 371 J . B. PRIDHAM

Wood Hemicelluloses: Part I1 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 410 T. E. TIMELL

VOLUME 21

Emil Fischer and His Contribution to Carbohydrate Chemistry . . . . . . . . . . . . . . . . . . . . . . 1 KARL FREUDENBERG Mass Spectrometry of Carbohydrate Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . N. K. KOCHETKOV AND 0. S. CHIZIIOV

39

TheGlycofuranosides ......................................................... 95 JOHN W. GREEN 95

xxii CONTENTS OF VOLUMES 1-53

Deoxy Sugars ................................................................ 143 STEPHEN HANESSIAN

Complexes of Alkali Metals and Alkaline-Earth Metals with Carbohydrates . . . . . . . . . . . 209 J. A. RENDLEMAN, JR.

Syntheticcardenolides ........................................................ 273 W. WERNER ZORBACH AND K. VENKATRAMANA BHAT

TheTeichoic Acids ............................................................ 323 A. R. ARCHIBALD AND J. BADDILEY

The Effects of Plant-Growth Substances on Carbohydrate Systems . . . . . . . . . . . . . . . . . . , 377 H. W. HILTON

Chemical Synthesis of Poiysaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 431 I. J. GOLDSTEIN AND T. L. HULLAR

VOLUME 22

Fred Smith(1911-1965) ....................................................... 1 REX MONTGOMERY

Acetolysis ................................................................... 11 R. D. GUTHRIE AND J. F. MCCARTHY

Acid-Catalyzed Hydrolysis of Glycosides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 25 J. N. BEMILLER

Neighboring-Group Participation in Sugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 109 LEON GOODMAN

Halogenated Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 177 J. E. G. BARNETT

o-Fructose and Its Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 229 L. M. J. VERSTRAETEN

TheMononucleotides...... .................................................... 307 TOHRU UEDA AND JACK J. Fox

X-Ray Structure of Polysaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 421 R. H. MARCHESSAULT AND A. SARKO

The Thermal Degradation of Starch . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 483 C. T. GREENWOOD 483

CONTENTS OF VOLUMES 1-53 xxiii

VOLUME 23

Clifford Burrough Purves(1902-1965) ........................................... 1 A. S. PERLIN

Mutarotation of Sugars in Solution: Part 1

History, Basic Kinetics, and Composition of Sugar Solutions ......................... WARD PIGMAN AND HORACE S. ~ S B E L ~

11

Application of the 0 x 0 Reaction to Some Carbohydrate Derivatives .................. ALEX ROSENTHAL

59

Cyclic Monosaccharides Having Nitrogen or Sulfur in the Ring ...................... 115 H. PAULSEN AND K. TODT

Sulfonic Esters of Carbohydrates: Part I ......................................... 233 D. H. BALL AND F. w. PARRlSH

Starch Degrading and Synthesizing Enzymes: A Discussion of Their Properties and Action Pattern .................................................. 281 C. T. GREENWOOD AND E. A. MILNF

Structural Chemistry of Fungal Polysaccharides ................................... 367 P. A. J. GORIN A N D J. F. T. SPENCER

Pyrolysis and Combustion of Cellulosic Materials .................................. 419 F. SIMFIZADEM

VOLUME 24

RichardKuhn(1900-1967) ..................................................... 1 HANS H. BAER

Mutarotation of Sugars in Solution: Part I I Catalytic Processes, Isotope Effects, Reaction Mechanisms, andBiochemica1 Aspects ....................................................... 13 HOKACE S. ISBELL AND WARD PIGMAN

TheNitroSugars ............................................................. 67 HANS H. BAER

Sulfonic Esters of Carbohydrates: Part I1 ......................................... 139 D. H. BALL AND F. W. PARR~SH

Unsaturated Sugars ........................................................... 199 R. J. FERRIER

xxiv CONTENTS OF VOLUMES 1-53

Structure, Conformation, and Mechanism in the Formation of Polysaccharide Gels and Networks ............................................ 267 D. A. REES

GumsandMucilages .......................................................... 333 G. 0. ASPINALL

Glycosphingolipids (Sugar-Sphingosine Conjugates) ................................................ 381 J. KISS

Protein-Carbohydrate Compounds in Human Urine ............................... 435 E. H. F. MCGME

VOLUME 25

Stanley Peat (1902-1969). ...................................................... 1 J. R. TURVEY

Gel Chromatography of Carbohydrates .......................................... SHIRLEY C. CHURMS

13

Crystal-Structure Data for Simple Carbohydrates and Their Derivatives ......................................................... 53 GERALD STRAHS

Oxirane Derivatives of Aldoses .................................................. 109 NEIL R. WILLIAMS

2,s-Anhydrides of Sugars and Related Compounds ................................. 181 J. DEFAYE

Alditol Anhydrides ............................................................ 229 S. SOLTZBERG

TheSugarsofHoney .......................................................... 285 I. R. SIDDIQUI

Reactions of Free Sugars with Aqueous Ammonia.. ................................ 311 M. J. KORT

Synthesis of Nitrogen Heterocycles from Saccharide Derivatives ...................... 351 HASSAN EL KHADEM

Aspects of the Structure and Metabolism of Glycoproteins .......................... 407 R. D. MARSHALL AND A. NEUBERGER

CONTENTS OF VOLUMES 1-53 xxv

VOLUME 26

Melville Lawrence Wolfrom (1900-1969) ......................................... DEREK HORTON

1

Conformational Analysis of Sugars and Their Derivatives ........................... 49 PHILIPPE L. DURETTE AND DEKEK HORTON

Cyclic Acyloxonium Ions in Carbohydrate Chemistry .............................. 127 HANS PAULSEN

Cyclic Acetals of Ketoses ....................................................... 197 ROBERT F. BRADY, JR.

Tables of the Properties of Deoxy Sugars and Their Simple Derivatives ................ 279 ROGER F. BUTTERWORTH AND STEPHEN HANESSIAN

Morphology and Biogenesis of Cellulose and Plant Cell Walls ........................ 297 F. SHAFIZADEH AND G. D. MCGINNIS

Biosynthesis of Saccharides from Glycopyranosyl Esters of Nucleoside Pyrophosphates (Sugar Nucleotides) ........................................... 351 H. N~KAIDO AND W. Z. HASSID

VOLUME 27

William Werner Zorbach (191f~Y70) ........................................... 1 G. A. JAMIESON

Proton Magnetic Resonance Spectroscopy: Part 1 .................................. BRUCE COXON

7

Non-aqueous Solvents for Carbohydrates ......................................... 85 C. J. MOVE

Sugars Specifically Labeled with Isotopes of Hydrogen ............................. 127 J. E. G. BARNETT AND D. L. CORMA

The Use of Carbohydrates in the Synthesis and Configurational Assignments of Optically Active, Non-carbohydrate Compounds ................................ 191 T. D. INCH

The Wittig Reaction in Carbohydrate Chemistry .................................. 227 Yu. A. ZHDANOV, Yu. E. ALEXEEV, AND V. G. ALEXEEVA

Glycoenzymes: Enzymes of Glycoprotein Structure ................................ 301 JOHN H. PAZUR AND N. N. ARONSON. JK.

xxvi CONTENTS OF VOLUMES 1-53

VOLUME 28

Lbsz16 Vargha(1903-1971) ..................................................... 1 JANOS KUSZMANN

Applications of GasLiquid Chromatography toCarb0hydrates:PartI ....................................................... 11 GUY G. S. DUTTON

Dehydration ReactionsofCarbohydrates ......................................... 161 MILTON s. FEATHER AND JOHN F. HARRIS

Deoxyhalogeno Sugars ......................................................... 225 WALTER A. SZAREK

Glycosyl Esters of Nucleoside Pyrophosphates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 307 NICOLAI K. KOCHETKOV AND VLADIMIR N. SHIBAEV

a-o-Mannosidase ............................................................. 401 SYBIL M. SNAITH AND GUILDFORD A. LEVVY

VOLUME 29

BernardRandallBaker(1915-1971) ............................................. 1 LEON GOODMAN

Solutions to the Hidden-Resonance Problem in Proton Nuclear Magnetic Resonance Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . LAURANCE D. HALL

11

Mass Spectrometry in Structural Analysis of Natural Carbohydrates . . . . . . . . . . . . . . . . . 41 J ~ R G E N LONNGREN .AND SICFRlD SVENSSON

The Electrochemistry of Carbohydrates and Their Derivatives . . . . . . . . . . . . . . . . . . . . . . . 107 MICHALFEDOROGKO

Synthesis and Utilization of Formose Sugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173 TAKASHI MIZUNO AND ALVIN H. WEISS

P-Eliminative Degradation of Carbohydrates Containing Uronic Acid Residues . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 230 JOSEPH Gss

Chemically Reactive Derivatives of Polysaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 305 JOHN F. KENNEDY

CONTENTS OF VOLUMES 1-53 xxvii

VOLUME 30

DavidJamesBell(1905-1972) .................................................. 1 JOHN S. D. BACON AND DAVID J. MANNERS

Applications of Gas-Liquid Chromatography to Carbohydrates: Par t I1 ............... GUY G. S. DUTTON

9

Structures and Syntheses of Aminoglycoside Antibiotics ............................ 11 1 SUMIO UMEZAWA

Biochemical Mechanism of Resistance to Aminoglycosidic Antibiotics ................. 183 HAMAO UMEZAWA

The Metabolism of a,u-Trehalose ............................................... 227 ALAN D. ELBEIN

Application of Enzymic Methods to the Structural Analysis of Polysaccharides: Part I .............................................. 257 J. JOHN MARSHALL

Dextrans .................................................................... 371 RAMON L. SIDEBOTHAM

Bibliography of Crystal Structures of Carbohydrates, Nucleosides, andNucleotides 1970-1972 ..................................................... 445 GEORGE A. JEFFREY AND MUTTAIYA SUNDARALIFIGAM

VOLUME 31

Hewitt Grenville Fletcher, Jr. (1917-1973) ........................................ CORNELIS P. J. GLAUUEMANS

1

Deamination of Carbohydrate Amines and R'elated Compounds ...................... J. MICHAEL WILLIAMS

9

The Reaction of Ammonia with Acyl Esters of Carbohydrates ....................... 81 MARIA E. GELPI AND RAUL A. C A ~ E N A S

Chemistry and Biochemistry of Apiose ........................................... 135 RONALD R. WATSON AND NEIL S. ORENSTEIN

Specific Degradation of Polysaccharides .......................................... 185 BENGT LINDBERG, JORGEN L~NNGREN, AND SIGFRID SVENSSON

Chemistry and Interactions of Seed Galactoniannans ............................... 241 IAN C. M. DEA AND ANTHONY MORRISON

xxviii CONTENTS OF VOLUMES 1-53

The Interaction of Homogeneous, Murine Myeloma Immunoglobulins with Polysaccharide Antigens ................................................... 313 CORNELIS P. J. GLAUDEMANS

Bibliography of Crystal Structures of Carbohydrates,

GEORGE A. JEFFREY AND MUTTAIYA SLINDARALINGAM Nucleosides, and Nucleotides, 1973 .............................................. 347

VOLUME 32

William Zev Hassid (1899-1974) ................................................ 1 C L ~ T O N E. BALLOU AND HORACE A. BARKER

Dithioacetals ofsugars ........................................................ 15 JOSEPH D. WANDER AND DEREK HORTON

TheUtilizationofSugarsbyYeasts .............................................. 125 JAMES A. BARNETT

Noncytotoxic, Antitumor Polysaccharides ......................................... 235 ROY L. WHISTLER, ALFRED A. BUSHWAY, PREM P. SMGH, WARO NAKAHARA, AND REIKO TOKUZEN

Hemieellulases: Their Occurrence, Purification,

ROBERT F. H. DEKKER AND GEOFFREY N. RICHARDS Properties,andModeofAction ................................................. 277

Bibliography of Crystal Structures of Carbohydrates,

GEORGE A. JEFFREY AND MUTTAIYA SUNDARALMGAM Nucleosides, and Nucleotides, 1974 .............................................. 353

VOLUME 33

Alfred Gottschalk (1894-1973) .................................................. 1 ALBERT NEUBERGER

Relative Reactivities of Hydroxyl Groups in Carbohydrates ......................... 11 ALAN H. HAINES

Synthesis of Naturally Occurring C-Nucleosides, Their Analogs,

STEPHEN HANESSIAN AND ANDRB G. PERNET and Functionalized C-Glycosyl Precursors ........................................ 11 1

Reactions of ~-Glucofuranurono-6,3-~actone ...................................... 189 KARL DAX AND HANS WEIDMANN

CONTENTS OF VOLUMES 1-53 xxix

TheChemistryofSucrose ...................................................... 235 k A Z KHAN

The Pneumococcal Polysaccharides: A Re-examination . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 295 OLLE LARM AND BENGT LINDBERC

Pectic Enzymes ............................................................... 323 ~ B O M ~ R A REXOVA-BENKOVA AND OSKAR MARKOVI~.

Bibliography of Crystal Structures of Polysaccharides 1967-1974 . . . . . . . . . . . . . . . . . . . . 387 ROBERT H. MARCHESSAULT AND PUDUPADI R. SUNDARARAJAN

VOLUME 34

EdwardJohnBourne(1922-1974) ............................................... 1 HELMUT WEIGEL

1,6-Anhydro Derivatives of Aldohexoses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . , . . 23 MILOSLAV ~ E R N Y AND JAN STANEK, JR.

Cyclic Acetals of the Aldoses and Aldosides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 179 ANTHONY N. DE BELDER

The Koenigs-Knorr Reaction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 243 KIKUO IGARASHI

Metabolism of D-Fructose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 285 MNSHEN CHEN AND ROY L. WHISTLER

Bibliography of Crystal Structures of Carbohydrates, Nucleosides, and Nucleotides, 1975 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . GEORGE A. JEFFREY AND MUTTAIYA SUNDARALINGAM

. . . . 345

VOLUME 35

Edmund Langley Hirst (1898-1975) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . MAURICE STACEY AND DAVID J. MANNERS

1

CarbohydrateBoronates ....................................................... 31 ROBERT J. FERRIER

Biosynthesis of Sugar Components of Antibiotic Substances . . . . . . . . . . . . . . . . . . . . . . . . . HANS GRISEBACH

81

The Lectins: Carbohydrate-Binding Proteins of Plants and Animals . . . . . . . . . . . . . . . . . . 127 IRWIN J. GOLDSTEIN AND COLLEEN E. HAYES

xxx CONTENTS OF VOLUMES 1-53

Biochemistry of Plant Galactomannans . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 341 PRAKASH M. DEY

Bibliography of Crystal Structures of Polysaccharides, 1975 . . . . . . . . . . . . . , . . . . . . . . . . . 377 PUDUPADI R. SUNDARARAJAN AND ROBERT H. MARCHESSAULT

VOLUME 36

JohnArcherMills(1919-1977) .................................................. 1 STEPHEN J . ~ G Y A L

Joseph VincentKarabinos(192~1977) ........................................... 9 WENDELL W. BINKLEY

Nutritive Sweeteners Made from Starch . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ROBERT V. MACALLISTER

15

Glycosiduronic Acids and Related Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . DINA KECLEVI~

57

The Synthesis of Polynucleotides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 135 MORIO IKEHARA, EIKO OHTSUKA, AND ALEXANDER F. MARKHAM

The Hemicelluloses of Grasses and Cereals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 215 KENNETH C. B. WILKIE

Exocellular, Microbial Polysaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 265 PAUL A. SANDFORD

Bibliography of Crystal Structures of Polysaccharides, 1976 . . . . . . . . . . . . . . . . . . . . . . . . . 315 PUDUPADl R. SUNDARARAJAN AND ROBERT H. MARCHESSALTLT

VOLUME 37

William Ward Pigman (1910-1977) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ANTHONY HEW

1

Free-Radical Reactions of Carbohydrates as Studied by Radiation Techniques . . . . . . . . . CLEMENS VON SONNTAG

7

Synthesis of L-Ascorbic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 79 THOMAS C. CRAWFORD AND SALLY ANN CRAWFORD

Primary Structure of Glycoprotein Glycans: Basis for the Molecular Biology of Glycoproteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 157 JEAN MONTREUIL

CONTENTS OF VOLUMES 1-53 xxxi

Neoglycoproteins: The Preparation and Application of Synthetic Glycoproteins ......... 225 CHRISTOPHER P. STOWELL AND YUAN CHUAN LEE

Biochemistry of a-D-Galactosidic Linkages in the Plant Kingdom ..................... 284 PRAKASH M. DEY

Bibliography of Crystal Structures of carbohydrates, Nucleosides, and Nucleotides 1976 ............................................... 373 GEORGE A. JEFFREY AND MUTTAIYA SUNDARALINGAM

VOLUME 38

EmilHardegger(1913-1978) ................................................... 1 HASSAN S. EL KHADEM

Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Polysaccharides ............. 13 PHILIP A. .I. GORIN

Photochemical Reactions of Carbohydrates ....................................... 105 ROGER W. BINKLEY

Fluorinatedcarbohydrates ..................................................... 195 ANNA A. E. PENGLIS

The Gulono-1,4-lactones: A Review of Their Synthesis, Reactions, and Related Derivatives .............................................. 287 THOMAS C. CRAWFORD

The Chemistry and Biological Significance of 3-Deoxy-o-rnanno-2-octu~osonic Acid (KDO) ...................................... 323 FRANK M. UNGER

Methylation Techniques in the Structural Analysis ofGlycoproteinsandGlycolipids ................................................ 389 HEIKKI RAUVALA, JUKU FINNE, TOM KRusius, JORMA KARKKAINEN, AND JOHAN JARNEFELT

Bibliography of Crystal Structures of Carbohydrates, Nucleosides, andNucleotides:1977and1978 ................................................. 417 GEORGE A. JEFFREY AND MUTTAIYA SUNDARALINGAM

VOLUME 39

KarlPaulGerhardtLink(1901-1978) ............................................ 1 CLINTON E. BALLOU

xxxii CONTENTS OF VOLUMES 1-53

The Selective Removal of Protecting Groups in Carbohydrate Chemistry .............. ALAN H. HAINES

13

The Reactivity of Cyclic Acetals of Aldoses and Aldosides ........................... 71 JACQUES GELAS

Synthesis and Polymerization of Anhydro Sugars .................................. 157 CONRAD SCHUERCH

The ChemistryofMaltose ...................................................... 213 RLU KHAN

Chemistry and Biochemistry of D- and L-Fucose ................................... 279 HAROLD M. FLOWERS

The Utilization of Disaccharides and Some Other Sugars by Yeasts ................... JAMES A. BARNETT

Affinity Chromatography of Macromolecular Substances on Adsorbents Bearing Carbohydrate Ligands ....................................... 405 JOHN H. PAZUR

VOLUME 40

The Synthesis of Sugars from Non-carbohydrate Substrates ......................... ALEKSANDER ZAMOJSKI, ANNA BANASZEK, AND GRZEGORZ GRYNKIEWICZ

1

Chemistry, Metabolism, and Biological Functions of Sialic Acids ..................... 131 ROLANDSCHAUER

Biosynthesis and Catabolism of Glycosphingolipids ................ Yu-TEH LI AND SU-CHEN Lr

The Lipid Pathway of Protein Glycosylation and Its Inhibitors:

RALPH T. SCHWARZ AND ROELF DATEMA The Biological Significance of Protein-Bound Carbohydrates .....

Bibliography of Crystal Structures of Polysaccharides 1977-1979 ................................. PUDUPADI R. SUNDARARAJAN AND ROBERT H. MARCHESSAULT

VOLUME 41

..........

..........

..........

John Kenyon Netherton Jones (1912-1977) ............................. WALTER A. SZAREK, MAURICE STACEY, AND GEORGE W. HAY

.. 235

.. 287

.. 381

.... 1

CONTENTS OF VOLUMES 1-53 xxxiii

Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Monosaccharides . . . . . . . . . . . . KLAUS BOCK AND CHRISTIAN PEDERSEN

27

Structural Chemistry of Polysaccharides from Fungi and Lichens . . . . . . . . . . . . . . . . . . . . 67 ELIANA BARRETO-BERGTER AND PHILIP A. J. GORIN

Biosynthesis of Cellulose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105 DEBORAH P. DELMER

Capsular Polysaccharides as Human Vaccines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 155 HAROLD J. J E N N ~ G S

High-Resolution, 'H Nuclear Magnetic Resonance Spectroscopy as a Tool in the Structural Analysis of Carbohydrates Related to Glycoproteins . . . . . . . . JOHANNES F. G. VLIEGENTHART, LAMBERTUS DORLAND, AND HERMAN VAN HALBEEK

... 209

VOLUME 42

DexterFrench(1918-1981) ..................................................... 1 JOHN H. PAZUR

The Composition of Reducing Sugars in Solution . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . STEPHEN J. ANGYAL

15

SynthesisofBranched-Chain Sugars ............................................. 69 JUJI YOSHIMURA

Sugar Analogs Having Phosphorus in the Hemiacetal Ring . . . . . . . . . . . . . . . . . . . . . . . . . . 135 HlROSHl YAMAMOTO AND SABURO INOKAWA

Carbon-13 Nuclear Magnetic Resonance Data for Oligosaccharides . . . . . . . . . . . . . . . . . . . 193 K L A U S BOCK, CHRISTIAN PEDERSEN, A N D HENRIK PEDERSEN

Ketonucleosides .............................................................. 227 KOSTAS ANTONAKIS

Plant Cell Walls .............................................................. 265 PRAKASH M. DEY AND KEN BIUNSON

L-Arabinosidases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 383 AKlU h J l

VOLUME 43

Natural-Abundance, "C Nuclear Magnetic Resonance-Spectral Studies of Carbohydrates Linked to Amino Acids and Proteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 KlLlAN DILL, ELISHA BERMAN, AND ANDRB A. PAVIA

xxxiv CONTENTS OF VOLUMES 1-53

Structure and Biological Activity of Heparin ...................................... BENITO CAW

51

Synthetic N- and 0-Glycosyl Derivatives of L-Asparagine, L-Serine, and L-Threonine ...................................................... 135 HAM G. GARG AND ROGER W. JEANLOZ

Bibliography of Crystal Structures of Carbohydrates, Nucleosides, and Nucleotides for 1979 and 1980; Addenda and Errata for 1970-1978; andIndexfor1935-1980 ....................................................... 203 GEORGE A. JEFFREY AND MUTTAIYA SUNDARALINGAM

VOLUME 44

FredShafuadeb,1924-1983 .................................................... GARY D. MCGINNIS

VibrationalSpectraofCarbohydrates ............................................ MOHAMED MATHLOUTHI AND JACK L. KOENIG

Monosaccharide Isothiocyanates and Thiocyanates: Synthesis, Chemistry, and Preparative Applications ......................................... ZBIGNIEW J. WITCZAK

Enzymic Analysis of Polysaccharide Structure ..................................... 147 BARRY V. MCCLEARY AND NORMAN K. MATHESON

Biosyntbesis of Bacterial Polysaccharide Chains

VLADIMIR N. SHIBAEV Composed of Repeating Units ................................................... 277

Lipid-Linked Sugars as Intermediates in the Biosynthesis

RAFAEL PONT LEZICA, GUSTAVO R. DALEO, AND PRAKASH M. DEY of Complex Carbohydrates in Plants ............................................. 341

Glycolipids of Marine Invertebrates ............................................. 387 NICOLAI K. KOCHETKOV AND GALINA P. SMIRNOVA

VOLUME 45

Burckhardt Helferich, 1887-1982 ............................................... 1 HERMANN STETTER

Francisco Garcia Gonzalez, 1902-1983 ........................................... 7 ANTONIO G6MEZ-SANCHEZ AND JOSE FERNANDEZ-BOLAROS

CONTENTS OF VOLUMES 1-53 xxxv

F.a.b.-Mass Spectrometry of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ANNE DELL

19

The Circular Dichroism of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . W. CURTIS JOHNSON, JR.

73

Proton Spin-Lattice Relaxation Rates in the Structural Analysis of Carbohydrate Molecules in Solution . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 125 PHOTIS DAIS AND ARTHUR S. PERLIN

I3C Nuclear Magnetic Resonance-Spectral Studies of Labeled Glycophorins . . . . . . . . . . . . 169 KILIAN DILL

The Chemistry and Biochemistry of the Sweetness of Sugars . . . . . . . . . . . . . . . . . . . . . . . . . 199 CHEANG-KUAN LEE

VOLUME 46

KonoshinOnodera,1910-1983 .................................................. 1 TOIiRU KOMANO AND NAOKI G S H I M U R A

VenancioDeulofeu,1902-1984 .................................................. 11 ROSA M. DE LEDERKREMER AND EDUARDO G. GROS

High-Performance Liquid Chromatography of Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . KEVIN B. HICKS

17

NMR Spectroscopy of Fluorinated Monosaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . RENE CSUK AND BRIGITTE I. GLANZER

73

Applications of Photosensitive Protecting Groups in Carbohydratechemistry ...................................................... 179 URI ZEHAVI

Inclusion Complexes of the Cyclomalto-oligosaccharides (Cyclodextrins) . . . . . . . . . . . . . . 205 RONALD J. CLARKE, JOHN H. COATES, AND STEPHEN F. LINCOLN

Hydrolysis and Other Cleavages of Glycosidic Linkages in Polysaccharides . . . . . . . . . . . . 251 CHRISTOPHER J. BIERMANN

Aqueous, High-Temperature Transformation of Carbohydrates Relative to Utilization of Biomass . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 273 OLOF THEANDER AND DAVID A. NELSON

Addendum to Article 3: References Published after 1986 (AddedatProofStage) ........................................................ 327 KEVIN B. HICKS

xxxvi CONTENTS OF VOLUMES 1-53

AddendumtoArticle4 ........................................................ 331 RE& CSUK AND BRIGITTE I. GLANZER

AddendumtoArticle6 ........................................................ 333 RONALD J. CLARKE, JOHN H. COATES, AND STEPHEN F. LINCOLN

VOLUME 47

Complexes of Metal Cations with Carbohydrates in Solution ......................... 1 STEPHEN J. ANGYAL

Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry ..................... IGOR TVAROSKA AND TOMAS BLEHA

45

13C Nuclear Magnetic Resonance-Spectral Studies of the Interactions of Metal Ions with Carbohydrates: Use of Relaxation Probes ................................ 125 KILIAN DILL AND R. DOUGLAS CARTER

Application of Anhydrous Hydrogen Fluoride for the Structural Analysis of Polysaccharides ........................................... 167 YURIY A. KNIREL, EVGENY V. VINOGRADOV, AND ANDREW J. MORT

The Thermal Decomposition of Carbohydrates. Part I. The Decomposition of Mono-, Di-, and Oligo-saccharides ............................................... 203 PIOTR TOMASIK, MIECZYSKAW PALASINSKI, AND STANISLAW WIEJAK

The Thermal Decomposition of Carbohydrates. Part 11. The Decomposition of Starch ................................................... 279 PIOTR TOMASIK, STANISLAW WIEJAK, AND MIECZYSLAW PALASINSKI

The Macrostructure of Mucus Glycoproteins in Solution ............................ 345 STEPHEN E. HARDING

VOLUME 48

HamaoUmezawa,1914-1986 ................................................... 1 TSUTOMU TSUCHIYA, KENJI MAEDA, AND DEREK HORTON

Chemistry of Carba-sugars (Pseudo-sugars) and Their Derivatives ................... TETSUO SUAMI AND SEIICHIRO OGAWA

21

Chemistry and Developments of Fluorinated Carbohydrates ......................... 91 TSUTOMU TSUCHIYA

Components of Bacterial Polysaccharides ......................................... 279 BENGT LINDBERG

CONTENTS OF VOLUMES 1-53 xxxvii

Glycoside Hydrolases: Mechanistic Information from Studies with Reversible and Irreversible Inhibitors ............................................ 319 GUNTER LECLER

VOLUME 49

Rezs8 Bognar, 1913-1990 ...................................................... 3 A N D ~ S LIPTAX, PAL NANASI, AND FERENC SZTARICSKAI

Jean Emile Courtois, 1907-1989 ................................................. FRANCOIS PERCHERON

11

The Composition of Reducing Sugars in Solution: Current Aspects ................... 19 STEPHEN J. ANCYAL

Radical-Mediated Brominations at Ring Positions of Carbohydrates .................. 37 LASZLO SOMSAK AND ROBERT J. FERRIER

1,4:3,6-Dianhydrohexitols ...................................................... 93 PETER STOSS AND REINHARD HEMMER

Enzymic Methods in Preparative Carbohydrate Chemistry .......................... 176 SERGE DAVID, CLAUDINE AucB, AND CHRISTINE GAUTHERON

Structure of Collagen Fibril-Associated, Small Proteoglycans ofMammalian Origin ......................................................... 239 HARl GARC AND NANCY LYON

VOLUME 50

How Emil Fischer Was Led to the Lock and Key Concept for Enzyme Specificity ................................................. RAYMOND U. LEMIELJX AND ULRIKE SPOHR

1

Anomeric-Oxygen Activation for Glycoside Synthesis: The Trichloroacetimidate Method ............................................... 21 RICHARD R. SCHMIDT AND W~LLY ~ Z Y

SyntheticReactionsofAldonolactones ........................................... 125 ROSA M. DE LEDERKREMER AND OSCAR VARELA

Molecular Structure of Lipid A, the Endotoxic Center of Bacterial Lipopolysaccharides ................................................ 211 ULRICH ZAHRINCER, BUKO LINDNER, AND ERNST TH. RIETSCHEL

xxxviii CONTENTS OF VOLUMES 1-53

Developments in the Synthesis of Glycopeptides Containing

HARI G. GARG, KARSTEN VON DEM BRUCH, AND HORST KUNZ Glycosyl L-Asparagine, L-Serine, and L-Threonine ................................. 277

Physicochemical Analyses of Oligosaccharide Determinants of Glycoproteins ........... 311 ELIZABETH F. HOUNSELL

VOLUME 51

HoraceS.Isbell,1898-1992 ..................................................... 1 HASSAN S. EL KHADEM

Carbon-Proton Coupling Constants in the Conformational Analysis of Sugar Molecules .................................................... IGOR TVAROSKA AND FRANCOIS R. TARAVEL

15

Carbon-13 Nuclear Magnetic Relaxation and Motional Behavior of Carbohydrate Molecules in Solution ............................................. 63 PHOTlS DAIS

Mechanisms in the Glucansucrase Synthesis of Polysaccharides and Oligosaccharides from Sucrose .................................................. 133 JOHN F. ROBYT

The Variable Surface Glycolipids of Mycobacteria: Structures, Synthesis of Epitopes, and Biological Properties ................................... 169 GERALD 0. ASPINALL, DELPHI CHATTERJEE, AND PATRICK J. BRENNAN

Nonconventional Methods of Modification of Starch .................. PIOTR TOMASIK AND MARK F. ZARANYIKA

VOLUME 52

MauriceStacey,1907-1994 ....................................... PAUL FTNCH AND W. GEORGE OVEREND

Nomenclature of Carbohydrates ..................................

Thioglycosides as Glycosyl Donors in Oligosaccharide Synthesis ........ PER J. GAREGG

....... 243

............ 1

............ 47

............ 179

DihexuloseDianhydrides ....................................................... 207 MERILYN MANLEY-HARRIS AND GEOFFREY N. RICHARDS

Sugars and Nucleotides and the Biosynthesis of Thiamine ........................... 267 SERGE DAVID AND BERNARD ESTRAMAREIX

RENCASWAMI CI-IANDRASEKARAN

Sucrose Decomposition in Aqueous Solution and Losses in Sugar Manufacture and Refining ..................................... MARGARET A. CLARKE, LESLIE A. EDYE, AND GILI I A N EGGLESTON

CONTENTS OF VOLUMES 1-53 xxxix

Molecular Architecture of Polysaccharide Helices in Oriented Fibers ................. 311

..

VOLUME 53

John E.Hodge,1914-1996 .......................................... MILTON S. FEATHER

AlleneR.Jeanes,1906-1995 ......................................... NINA M. ROSCHER AND PAUL A. SANDFORD

HarrietL.Frush,1903-1996 ......................................... HASSAN S. EL KHADEM

Applications of Tin-Containing Intermediates to Carbohydrate Chemistry T. BRUCE GRINDLEY

..

......... 441

......... 1

......... I

Synthetic Applications of Selenium-Containing Sugars ............................ ZBIGNIEW J. WITCZAK AND STANISLAS CL~RNECKI

Anti-carbohydrate Antibodies with Specificity for Monosaccharide and Oligosaccharide Units of Antigens ............................................. JOHN H. PAZUR

Complexes of Starch with Inorganic Guests ..................................... PIOTR TOMASIK AND CHRISTOPHER H. SCtIILLINCI

Complexes of Starch with Organic Guests ...................................... PIOTR TOMASIK AND CHRISTOPHER H. SCHILLING

..

..

13

117

143

201

263

345

SUBJECT INDEX

Boldface numc~ruls indicate volume n 1 4 n 1 h w

A

Aaptos papillulu lectins, isolation and

Abequose, 21:187, 180-190, 23:272, properties, 35:3 16

SO: 173-1 74 2- and 4-O-methyl-, synthesis of. 30:23 ester of cytidinc pyrophosphate, isolation of,

gas-liquid chromatography of, 28:Oi residues in lipopolysaccharides, 26:42 I

2 8 3 16

Abequoside, methyl p-, 23:272 Abramov reaction, 3 4 9 8 Abrin

carbohydrate-binding specificity, 3S:255 immunization 10 toxic, 35: I29 isolation and purification, affinity

chromatography, 35: 138 purification and properties, 35:254 257

.4 h m r precutorius lectin, see Abrin seed extracts, hemagglutinating and toxlc

activities, 35:254-257 Abscission, 21:429 Acut~rhamoebcr. cellulose biosynthesia. 41 : I 08,

Acarbose, 48:24-25, 348 128

inhibition of sucrase by, 48:88 synthesis, 48:84

Acceptor products. structures, 51: 15 I I 55 Acceptor reaction, 51 : 15 I - I52

applications, 51: 162-163 Aceric acid. 4S:67 Accsulfame-K, 45:299 Acetalation, see also Acetonation

I ,2-acetoxonium ion in, 34: 190 by 2-acetoxypropene, 39:76 agents, 39:76 and aldonolactones, 50: 125-126 of 1,6-anhydrohexopyaiioses, 3 4 : W 03 catalysts, 39:80 of u-fructose, mechanism of; 26:? I X 220

Benzylidenation; Transacetalatioii

with enol ethers. 34:188 with gem-dihalides and base, 34: 188-1 90 ofhexoses and heuitols. 28:4 methods of, 26:211-218, 34:191 of nitro sugars, 24: I 16 principle governing, 34: 180-1 82 selective. 33:71 -72 of i -sorbose, mechanism of. 26:205

Acetaldehyde. 46:32 1 i n aqueous solution. 42:30 reaction with ii-allose, 34: 183-1 84 formation, 51 :28 1

acetolysis, 22: 12, 39324-26 of alditols. mass spectrometry of. 29:75-77 aldofuranoside formation from, 21:l I I alkyl monothio-, fonnation in

demercaptalation. 32:69

Acetals

preparation of, 32:72 ofanhydroalditols, fonnation and behavior

of2.5-aiih~droaldoses, synthesis of. 33: 126 benzylidene, reaction with .Y-

bicyclic. hydrogenolysis. 39: 133 carbohydrate

29:43

of, 25:205

bromosuccinimide. 26: 163-1 68

mass spectrometry and configuration of,

photochemical reactions. 38: 142 -147, 170 cleavage of p-nitro. 24: 125 cyclic

acetobroiiiinolysis, 39: 1 I4 Grignard reagent cleavage, 39: I53 halogenation, 39:95-121. 115-121 hydrogenolysis, 39:121-138, 136-138 maltose derivatives, 393237-238 migration, 39: I I 5 oxidation by chromium trloxlde,

39:82-85 oxidation by potassium permanganate,

39:82 oxidation by triphenylrnethyl

fluoroborate, 39:85 86

I

2 SUBJECT INDEX

Acetals (uintinued) ozonolysis, 39:8 1-82 peroxide-induced rearrangement,

photolysis, 39:86-95 polymerization, 39: I52 as protecting groups, and as functional

groups, 39:155-156 reaction with bromine, 39: 1 18 reaction with dibromomethyl methyl

ether, 39:119-121 reaction with hydrogen fluoride,

39:117 reaction with N-bromosuccinimide,

39:96-107 reaction with N-chlorosuccinimide,

39:118 reaction with 1,3,5-trichloro- 1,3,5-

triazine-2,4,6-trionc, 39: 1 18 reaction with triphenylmethyl

fluoroborate, 39: 107-1 13 reactivity, of aldoses and aldosides,

39:71-156 synthesis, 39:73

acetolysis of, 34:206 of aldoses and aldosides, 34: 179-24 I applications of, 34:207-209 cleavage by trityl fluoroborate, 34:207 conformational analysis of, 34: 197 con formational eq u i I i bna of.

degradation of, 34:8 diastereoisomerism of, 34: 195-197 formation of, 34: 180-1 82 hydrogenolysis of, 34:205 hydrolysis by acids, mechanism of,

mass spectrometry and structure of,

methanolysis of, 34:206 migration in, 34:205 nuclear magnetic resonance

39: 150

34: 198-202

34:202

34~192-194

spectroscopy and structure of, 34: 195-198

oxidation of, 34:207 ozonolysis of, 34:207 photolysis of, 34:207 reactions with N-bromosuccinimide,

synthesis of, 34:8, 182-192 34:206

from alditols, 36:4 of the aldoses and aldosides. 20:219-302 di-, hydrolysis of, 34:203-204 of ketoses, 26:197-277

hydrolysis of, 26:203 preparation of, 26: 199

of sucrose, 33:255 selective etherification of, 33:53

stability of. 26:202 sugar, conformations of, 26: 1 I X

of o-fructose, 22:245 esters and ethers, 22:289-290

dithio- acetylated, gas-liquid chromatography of,

28:66, 12 I acylation of, 32:45

conformations of, 32:9&92 formation and reactions of alkylidene

acetals of, 32:52-55 formation of, 32:17-19 glycosides and thioglycosides from,

history, 32: 16-17 Iiydrogenolysis by Raney nickel,

mass spectrometry of, 32:2 ~7 methylation of, 32:47 micro method of preparation of, 32:96 nucleophilic reactions, 32:3743 oxidation of hydroxyl groups in sugar

oxidation of sulfur atoms of. 32:82-88 physical constants of alduronic acids

and derivatives, 32: 1 16- I I8 physical constants of discaccharides and

their peracetates. 32: 1 I6 physical constants of substituted

monosaccharides, 32: 1 18-1 23 physical constants of unsubstituted

monosaccharides and their peracetates, 32: 102-1 I5

physical properties of, 32:98 reactions of amino groups in,

reactions of hydroxyl and other groups

reaction with bases, 32:57-60 replacement of alkylthio groups by

replacement of alkylthio groups by

32:66-70

32:75-7

residue, 32:8&82

32:55-57

in sugar, 32:44-60

halogens, 32:70-75

SUBJECT INDEX 3

mineral and Lewis acids, 32:60 70 spectroscopic properties of, 32:8X 98 ofsugars, 32:IS-123 sulfonic esters, fonnation and reaciions

of, 3248-52 in synthesis, 32: 16 tritylation of, 32:46

of 2-amino-2-deoxyaldoses, deamination

gas-liquid chromatography of, 30:33 glycoside synthesis by alcoholysis of

acyclic sugar. 34:244 mass spectra of sugar, 29:7 1-73 photolysis. 38: 150-1 53 selective esterification of carbohydrate,

selective methylation of carbohydraic.

sugar, 26: I3 in 1 -thioglycosiduronic acid prcparation,

of, 25: 192

33:4041

33:65-66

36: 10&102 exchange of, 34: 186-1 88, 192 gas-liquid chromatographic detemii nation

of hexitols, pentitols, and tetritols,

hydrolysis

of, 30:35

7: 137-207

(acid-catalyzed) of, 22:30, 59, I 13 selective, 39: 14-24

isomerization, 39:26-28 isopropylidene. in gas-liquid

chromatography, 28:37 mercaptalation of, 32:28 of monosaccharides, mass spcctra of,

nomenclature, 52: 123-1 24

of polyhydric alcohols, mass spectra of. 21:79

of polysaccharides, preparation of: 29:339 preparation

21:74

cyclic, 52:121-122

from dithioacetals, 32:65 from en01 ethers, 34: 1 88

propane- I ,3-diyl dithio-, preparation of,

protection as, 46: 182-1 X9 rearrangements of, 26:220 synthesis of, 34: 182-1 92 trimethylene dithio-, preparation of,

3 2 3 9

32: 37-38

w-deoxy sugars by catalytic reduction of, 21:176

Acetamide N-[5-( I ,2-dihydroxyethyl)-3-furyl]-.

formation of, 28:202 ~~,O-bis(trimethylsilyl)-. trimethylsilylation

with, 28:26 trifluoro-N-methyl-N-( trimethylsily1)-.

trimethylsilylation with, 28:28 trifluoro-N. 0-bis(triniethylsily1)-, as

trimethylsilylating agent, 28:27, 80 Acetamidodeoxyhexosidase, in Tay-Sachs

discasc, 31:6 Acetamido group

effect on acyloxoniurn rearrangements. 26:161

oligosaccharides containing, ' T - N M R data for, 42:209-2 I0

participation i n sugar reactions, 22: 127 Acetanilide, metabolism, 36:9 1 2-Acetate. trorworiented. nucleophilic attack

Acetates on carbonyl group, 51:7. 10

circular dichroism. 45: 120- 122 gas-liquid chromatography of

alditol, 30:30 -32 mass spectrometry of, 30:40

of methylated alditols, 30:89-98 of niethylated aldononitriles, 30: I00 of niethylated methyl glycosides. 30:26,

of methylated sugars, 30:29. 86

mass spectrometry of, aldononitrile.

82

methylated. 30:43 Acetic acid

(2,3-0-isopropylidene-P-r~-ribofuranosyl)-, ethyl ester, preparation of, 33:157

bromo-. cellulose ester, preparation of, 29:337

bromo (2,3,4,6-tetra-O-acety 1 -P-o- glucopyranosy1)-, methyl ester, preparation of, 33:146-147

as catalyst in osazone formation, 22:264 chloro-

as catalyst for polymerization of 1.6-

as solvent for sucrose, 27: 104

effect on sugarcane. 21 :427

anhydro sugars, 2 1 :486

(4-chloro-2-methy1phenoxy)-

4 SUBJECT INDEX

Acetic acid (continued) as herbicide, 21:392

substance, 21:398

substance, 21:398

substance, 21:398

46:22 1

(2-chlorophenoxy)-, as plant-growth



cyclodextrin inclusion complexes with,

(5-deoxy-5-adenosine-5-yl)-, 43:335 (2,4-dichlorophenoxy)-,

effect on sugarcane, 21:424 as herbicide, 21:392 metabolism by plant tissue, 21:396

(3,5-dichlorophenoxy)-, as herbicide, 21:394 ~~-(2,3-@isopropy~idene-p-~~-

ribofuranosy1)-, methyl ester, preparation of, 33:163

o~-tetrahydropyran-2-y1-, preparation of, 33:145

esterification of D-glucose with, 33:44 esters of sugar dithioacetals, preparation of,

ethoxylyfluoro-, ethyl ester, carbohydrate

(ethy1enedinitrilo)tetra-

32:45

substrate, 40:10&105

effect on a-amylase action, 30:286 inhibitor of protein glycosylation, 40:297

2-formyl-5-(hydroxymethyl)pyrrole- I-,

2-formyl-5-methylpyrrole-l-, formation of,

gas-liquid chromatographic determination

in hydrolysis of polysaccharides, 28: 17 iodo-, cellulose ester, preparation of, 29:338 liquid chromatography of, 46:53-54 pH of aqueous solutions of, 46:252 as solvent for sugars, 27: 102 (2,3,4,6-tetra-O-acetyl-~-~-g~ucopyranosyl)-,

trichloro-

formation of, 46:312-314

4 6 ~ 3 12-3 14

of, 30:36

preparation of, 33: 146-147

in hydrolysis of glycoproteins, 28: 17 as plant-growth substance, 21:402

effect on abscission and ripening, 21:429

as herbicide, 21:392

(2,4,5-trichlorophenoxy)-

on sugarcane, 21:424

trifluoro-

anhydride 1,6-anhydrohexopyranose cleavage by,

34:66 applications of, in carbohydrate

chemistry, 16:59-84 for hydrolysis of cyclic acetals, 34:205 in organic syntheses, 34:s

catalytic action on trimethylsilylation,

in hydrolysis of plant cell walls, 28: 16 28:25

(2,3,5-tri-O-benzoyl-a-~- and p-D- ribofuranosy1)-

ethyl esters, preparation of, 33: 156, 162 preparation of, 33: 162

(2,3,5-tri-O-benzyl-a-~- and p-D- ribofuranosy1)-, ethyl esters, preparation of, 33:158

triisopropylbensenesulfonyl chloride, in esterification of nucleosides, 33: 13

triphenylmethoxy-, anhydride with 2,4,6-

vinyl-, see 3-Butenoic acid Acetic acid-I4C, (2,4-dichlorophenoxy)-,

metabolism by plant tissue, 21:396 Acetic acid-sulfuric acid, cyclitol

rearrangement in, 26: 188-191 Acetic anhydride

in acetolysis, 22:11 reaction with amino group in dithioacetals,

zinc chloride, rearrangements of saccharides 32:55

in, 26: 192 N- Acetimidoyl groups, bacterial

polysaccharides, 48:307 Acetoacetic acid, ethyl ester, condensation

products with D-fructose, 22:288,305 Acetobacter suboxydans

in dendroketose synthesis, 42: 129 oxidative specificity toward aldose

dithioacetals, 32:81-82 selective oxidation of alditols with, 33: 100

cellulose assembly model, 41: 113 cellulose biosynthesis, 41:106-107, 116,

high-molecular-weight precursors,

lipid intermediates involvement,

Acetobacter xylinum

119, 124, 128

41:135-137, 141

41:132-133 Acetobrominolysis, 22:22

of cyclic acetals, 39: 1 14

SUBJECT INDEX 5

Acetohalogeno carbohydrates, 4 5 5 Acetohydroximate

1 -thio-P-D-ghcopyranosyl2-phenyl-.

1 -thio-2-phenyl-, biosynthesis of, 26:44 1

formation, 46:294 from hydrothermolyzed cellulose,

biosynthesis of, 26:441

Acetoin

46:304305 Acetol

formation of, 28:200,46:293 high-temperature transformation, in alkali

conditions, 46:284 Acetolysis, 22: 1 1-23

acetal, 39:24-26 of alkylthio groups of dithioacetals, 32:69 of aminodeoxy 1,6-anhydrohexopyranoses,

of 1,6-anhydrohexopyranoses, 34:65, 162 and anomerization, 31: 197-200 henzyl ethers, selective, 39:45 of cyclic acetals, 34:206 of cyclic monosaccharides, ring contraction

in degradation of polysaccharides,

and epimerization, 31:200 and f.a.b.-mass spectrometry, application to

preliminary screening of glycoproteins for sugar type, 45:5&5 1

34:128

in, 23: 187

31:197-200

glycosidic linkage cleavage, 46:269-270 monitoring with f.a.b.- mass spectrometry,

of monosaccharide derivatives, 22: I2 of polysaccharides, 22:20, 24:339 reagents, 39:25 rearrangements during, 22: 19 structural analysis, 38:396,409 of tragacanthic acid, 24:362 usefulness of, 22:21

Acetonation, see also Acetalation of D-allose, 34: 183 of o-galactose, 34: 185

of D-ribose, 34:18&185 of D-talose, 34: 184

enolization of, in water and in deuterium

photochemical cycloaddition with 3,4-6-tri-

45:49

Of D-ghlCOSe, 34: 182-183

Acetone

oxide, 24:29

0-acetyl-D-glucal, 38:106, 117 photochemical reaction with carbohydrate

acetals, 38: 143-145 reaction with methyl 2-0-methyl-~-

glucofuranoside, 30:4 solubility of sucrose in, 27: 107 solubility of sugars in, effect of zinc chloride

sugar and alditol compounds, 21: 19

cyclodextrin inclusion complexes with,

solvent for trimethylsilylation, 28:29 trichloro-

on, 27:95

Acetonitrile

46:221

intermediate in nucleotide formation,

as solvent for sugars, 27: 1 13 36: 157

Acetophenone a-(D-arabinofuran0syl)-p- methoxy-,

preparation of, 33: 154-155 a-(D-galactofuranosyl-p-methoxy)-,

preparation of, 33: 154-155 a-(D-glucofuranosy1)-p-methoxy-,

preparation of, 33: 154-155 (~-(2,3;5,6-di-0-isopropylidene-a-~-and p-D-

mannofuranosy1)-p-methoxy-, preparation of, 33:154-155

Acetoxonium ion in acetal preparation, 34:190 in mercaptalation, 32:32

Acetoxonium salts, 26: 130 Acetoxy group

22:181

122

displacement in carbohydrates by halogen,

participation in sugar reactions, 22: I 16,

Acetoxyl group elimination from peracetylated glycosides in

reactivity of, in acyloxonium salt formation, mass spectrometry, 29:46

26:131 Acetoxymethylpyran-2-one, 3-acetoxy-6-,

I -0-Acetyl, activation, 3-0-glycosidic linkage

1 -0-Acetyl-a-oi-carba-glucopyranose,

Acetylation

50: 165- 166

formation, 50:292-293

48:6 1-62

of alditols, effect of borate complexes on, 28:34

6 SUBJECT INDEX

Acetylation (continued) of amino sugars, effect on behavior in

of 1,6-anhydrohexopyranoses, 34:83 of carbohydrate boronates, 35:53 of o-fructose derivatives, 22:250 f.a.b.-mass spectrometry of, 45:53 of methyl glycosides, 30:26 of polysaccharides, 29:329-333

solution, 42:47

N-Acetyl-P-o-glucosamine antibodies,

N-Acetyl-P-o-glucosamine-1 -P, 53:252-253 Acetyl bromide, reaction with carbohydrates,

22:22 Acetyl chloride

53:230-23 1

chloro-, in esterification of thymidine, 33: 14 reaction with carbohydrates, 22:22

Acetyl chloridechlorodiphenyl-, in

Acetylcoenzyme A, from aerobic catabolism of

N-Acetyl-2,3-dehydroneuraminic acid, 48:35 1 N-Acetyl-9-deoxy-9-fluorone~uaminic acid,

Acetylene compounds, o-glucopyransoylation

Acetylenic precursors, for sugar syntheses,

Acetyl esterase, 44: 162 Acetylformoin, from dehydration of o-fructose,

28:176, 180 N-Acetylfucosamine, glycosidic linkages,

N-Acetylgalactosamine, trichloroacetimidates,

N-Acetyl-o-galactosamine, 47: 195, 200-20 1 Acetylgentiobiose, octa-0-, Helferich's work

N- Acetylglucosamine

esterification of thymidine, 33: 13

D-glucose, 32: 163

"C-NMR data for, 46: 177

of, 25:242

40:34

47: 195-196

synthesis, 50:84,93-98

on, 45:4

glycosidic, in glycoproteins, 46:257 linked to L-asparagine, N-glycosylic linkage,

naturally occurring glycosidic linkages,

residues, 47:181-182

46:255

50:61, 68

Acetylglucosaminidase H, endo-P-N-, 44:370 Acetyl group

determination of in carbohydrates, 26: 15 in N-polysaccharides, 29:343

effect on antitumor activity of

hindered rotation of, in monosaccharides,

N-Acetyl groups, gas-liquid chromatographic

N- Acetylhexosamines, glycosidic linkages,

Acetylimino group, monosaccharides

Acetylium ion

polysaccharides, 32:261

23:193, 197

determination of, 30:36

47: 188

containing, 23: 166

in acetolysis, 22: 1 1 in mass spectra of alditol acetates, 29:5 1

N-Acetyllactosamine, trichloroacetimidates,

N- Acetylmannosamine synthesis, 50:73,78-80

functional derivatives, 49:195, 197-199 synthesis of derivatives, 49:201-203

N-Acetylmuramic acid, circular dichroism,

Acetylneuraminic acid 45:113

N-, 48:114 biosynthesis, 49: 194195 circular dichroism, 45: 11 1-1 12 methyl a-and P-o-ketopyranosides,

circular dichroism, 45: 112 synthesis, 49:200

2-0-methyl a-N-, 51:97-98 a-(2+6)-linked N-Acetylneuraminic acid

Acetylpentopyranosylamines, 2,3,4-tri-0-,

2-AcetyIpyrrole, formation of, 46:3 12-3 13 1 -Acetylrubranitrose, 43:333 N-Acetyltetrapeptide, 51 :229 Acid anhydrides, in selective esterification of

carbohydrate, 33: 1 3 4 2 Acid chlorides, in selective esterification of

carbohydrate, 33: 1 3 4 2 Acid degradation, monosaccharides,

52:457459 Acid factor, 47:3 18 a-Acid glycoprotein

glycosides, synthesis, 48: 1 15

47:57

oligosaccharides, liquid chromatography

structural analysis, 43: 17-20

uronic acids in, 46:258

separation, 46:4243

Acid glycosaminoglycans, quantitation of

Acid hydrolysis di-o-fructose dianhydrides and per-O-methyl

SUBJECT INDEX 7

derivatives, 52:232 sucrose, 52:455456

Acidic sugars, 48:292-293 glyculosonic acids, 48:295-298 glycuronic acids, 48:293-295

Acid invertase in plant cell walls, 42:301 Acid phosphatase

Helferichs work on, 455 in plant cell walls, 42:301-302

a, P-unsaturated, chemical and physical Acids, see also specific types

properties, 27:260-267

a-keto, polarography of, 29: 147 carboxylic, as catalysts for mutarotation,

catalysis of mutarotation of sugars by,

catalytic coefficients for anions of weak,

in catalytic hydrolysis of glycosides, 22:25 effect on reducing sugars in solution, 42:34 hydroxy

of high optical purity, preparation of,

from hydrocellulose, mass spectrometry

synthesis by Wittig reaction, 27:253-260

24:27,34

24:14

24:17, 18

27: 199-20 1

of, 30:38 ketonucleoside stability in, 42:245-246 organic, as solvents and reaction media.

reactions of mineral, with dialkyl 21: 102

dithioacetals, 32:60 Ackers equation, 25:25 Aclacinomycins, 48: 10 Acofriose, L-, from Rhodopseudomonos

Aconitase, inhibition of, 22:210 Aconitic acid, 6:23 1-249 Acosamine

cupsulatu lipopolysaccharide, 29:67

N-acetyl-ix-, synthesis, 40:2425 N-acetyl-r-, synthesis, 40: 1 I5

Acrusieae, polysaccharides of, 23:368 Acridine Orange, 53:383-384

5-iodocyisylyl-(3+5)-guanosine, hydrate,

sodium cytidylyl-(3 +5 )-guanosine, crystal structure, 43:301

hexacosyhydrate, 43:335 a-Acritol, see Mannitol, DL- Acrocylindrium, crystalline endo-o-

galacturonanase from, 33:363

Acrolein acetal, hydrogenolysis and regioselectivity,

1,6-anhydrohexopyranoses from, 34: 1 12 Diels-Alder condensation and reduction of,

dimer, monosaccharides prepared from,

or-threonic acid synthesis, 40:5 r

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