Carbohydrate Research Vol. 372, 2013

Contents

FULL PAPERS

Synthesis

Theoretical study of the mutarotation of erythrose and threose: acid catalysis pp 1–8

Luis Miguel Azofra*, Ibon Alkorta, José Elguero

HOO

OH

OH

HO

O

OH

OH

CO

OH

OH

OH

O

OH

OH

OH

Non-reactiveopen-chain

Reactiveopen-chain TS Furanose

*

A convenient synthesis of N-linked diglycose derivatives based on one-pot tandem Staudinger/aza-Wittig/reductionand biological evaluation

pp 15–22

Pingzhu Zhang, Yinbo Li, Ming Liu, Yanfei Wang, Cuicui Li, Donglai Ma, Hua Chen, Kerang Wang, Xiaoliu Li*, Jinchao Zhang

R1

HN R2

R3

HN R4

R3N R4

AcR1 N3

R1, R2, R3, R4 = sugar moieties

Ph3P, THF, rt., 0.5 h.then R2-CHO, rt., 2 h;

thenNaBH3CN-AcOH,0oC, 0.5 h.

ii) NaOMe, MeOH,rt.;then 60% AcOH, 45 oC

NaOMe, MeOH, rt.;then 60% AcOH, 45 oC

i) AcCl, Et3N, CH2Cl2, 0 oC

A series of novel N-linked diglycose derivatives were conveniently and directly synthesized based on the key step of one-pot tandem Staudinger/aza-Wittig/reduction reactionfollowed by deprotection. Some compounds exhibited good cytotoxicity to A-549.

Preparation and application of a �clickable� acceptor for enzymatic synthesis of heparin oligosaccharides pp 30–34

Chao Cai, Kristi Edgar, Jian Liu, Robert J. Linhardt*

Heparosan

1. Depolymerization 2. Modification

OHO

HO

HOOCO

OHO

HO

OHN3

Application forchemozenzymatic reaction

OO

HO

HOOCO

OHO

HO

OHN3

OHO

HO

HOOC

OH

OOHO

TFAHN

HO

Tetrasaccharide as an acceptor with an "clickable" azido group

OOHO

OH

HOOCO

OHO

NHAcOH

OHO

HOHO

OH

HOOCO

OHO

AcHN

OH

n

iii

Contents lists available at SciVerse ScienceDirect

Carbohydrate Research

journal homepage: www.elsevier .com/locate /carres

Glycosylation of �basic� alcohols: methyl 6-(hydroxymethyl)picolinate as a case study pp 35–46

Shuai Wang, Dominique Lafont, Jani Rahkila, Benjamin Picod, Reko Leino, Sébastien Vidal*

Biochemistry and Enzymes

Tests for the mechanism of starch biosynthesis: de novo synthesis or an amylogenin primer synthesis pp 55–59

Rupendra Mukerjea, John F. Robyt*

Hydrolysis of konjac glucomannan by Trichoderma reesei mannanase and endoglucanases Cel7B and Cel5A for theproduction of glucomannooligosaccharides

pp 60–68

Atte Mikkelson, Hannu Maaheimo, Terhi K. Hakala*

Konjac mannan

Enzymatic hydrolysis

0 5 10 20 30 40 50 60 70 80 90 100Det

ecto

r res

pons

e

? ? ? ?

HPAEC-PAD of hydrolysate

Fractionation by SEC

0 5 10 20 30 40 50 60 70 80 90 100Retention time (min)

Det

ecto

r res

pons

e

Isolated, characterized mannoglucooligosaccharides

Identification by enzymatic hydrolysis, MSQ, NMR

Retention time (min)

HPAEC-PAD of fractions

Characterization, Naturalproducts

Carbohydrate derivatives from the roots of Brassica rapa ssp. campestris and their effects on ROS production andglutamate-induced cell death in HT-22 cells

pp 9–14

Qian Wu, Jin-Gyeong Cho, Dong-Sung Lee, Dae-Young Lee, Na-Young Song, Youn-Chul Kim, Kyung-Tae Lee, Hae-Gon Chung,Myung-Sook Choi, Tae-Sook Jeong, Eun-Mi Ahn, Geum-Soog Kim, Nam-In Baek*

O

OH

HO OOH

O

O

CH2OH

O

O

HOH2C

O

O

O

O

O

HOHO

OHO

O

CH2OH

O

O

HOH2C

O

O

O

O

OH

HOHO

OHCH

3

O

compound 2

compound 3

compound 6

AMTT reduction

Viab

ility

(%of

cont

rol)

0

20

40

80

100

60

Compound 6 (µM)

-Glutamate +Trolox

+ + ++- - - - - -- --

++

10 40 8020

120

***

*

BROS production

Fluo

resc

ence

(%of

cont

rol)

Glutamate0

50

100

200

500

150

Compound 6 (µM)

- +Trolox

+ + ++- - - - - -- --

++

10 40 8020

****

iv Contents / Carbohydrate Research 372 (2013) iii–vi

LC–MS/MS analysis of chitooligosaccharides pp 23–29

Jaehyun Kim, Jinhee Kim, Jangmi Hong, Sunyoung Lee, Sehwan Park, Ji-Hye Lee, Jeongkwon Kim*

RT: 0.00 - 40.02

10015.46 hit li h idchitooligosaccharides

90

80

e OH H

OH70

ance 16.74

14.06O

HH

660

unda H

O146

50e

Abu O

HO 12

45

40ativ

eOH NH2 n

23

30Rel

a

19.8912.442 H n

2010.87

10 65 H10

10.65

20.98

H

021.999.14

0 5 10 15 20 25 30 35 40Time (min)

0

Time (min)

Acyl glycosides lignans, coumarins, and terpenes from the stems of Erycibe obtusifolia pp 47–54

Zhao-zhen Liu, Zhi-lai Zhan, Fu Liu, Ya-nan Yang, Zi-ming Feng, Jian-shuang Jiang, Pei-cheng Zhang*

O O

H3CO

OO

OH

OHOH

OO

OHHO

ROO O

H3CO

OO

O

OHOH

HO

O

OHHO

RO OO

HO OH

O O

OHOH

OH

OHO

ROO

O

HO OH

O O

OHOH

OH

OHO

RO

6 R = sinapoyl 7 R= sinapoyl 8 R= syringoyl

9 R= syringoyl

346

7 9

10

81'

1''

O

OCH3

OH

OCH3

OCH3

OCH3

OHO

sinapoyl = syringoyl =

35

6

78 9

10

1'

1''

13

45

7

8910

11 12

13

1'1''

1 23

45

67

8910

11 12

13

1'1''

O(S)(R) (R)

O(S)

OH

OCH3

OCH3

H3CO

H3CO

OOO

HO OH

O

OH

OH

OH

RO

17

9

9'

7'1'

4'

4 2

2'

1''

1'''

O(S)(R) (R)

O(R)

OH

OCH3

OCH3

H3CO

H3CO

O1

7

9

9'

7'1'

4'

4 2

2'

1 R = H

2 R = syringoyl

3 R= sinapoyl

4 R = syringoyl

5 R= sinapoyl

OO

HO OH

O

OHOH

OH

RO

1''1'''

Preparative isolation and structural characterization of sucrose ester isomers from oriental tobacco pp 73–77

Chunxiao Jia, Yingying Wang, Yonghua Zhu, Chunping Xu, Duobin Mao*

O

OCCH3

R3O

R2O OR1 O

OOH

OH

OH

OH

R1= R2 = R3 = C CH2 CH

CH3

CH2 CH3

1 2 3 4

5

O

O

R1=

R3=

R2 = R3 =

or R1=

or

R2 = R3 =

R1= R2 =

C CH2 CH

CH3

CH2 CH3

1 2 3 4

5

O

C CH2 CH

CH3

CH2 CH3

1 2 3 4

5

O

C CH2 CH

CH3

CH2 CH3

1 2 3 4

5

O

C CH

CH3

CH2 CH3

O6 7 8

9

C CH2 CH

CH3

CH3

O10 11 12

12

C CH

CH3

CH3

O13 14

14

R3=C CH2 CH

CH3

CH2 CH3

1 2 3 4

5

R 1= R2 =

O

C CH

CH3

CH2 CH3

O6 7 8

9

STE III:

sucrose tetraester(STE)

STE :

STE I:

ultrasonic-assistedextraction

semi-preparative RP-HPLC

NOTES

Polysaccharides

Structure of the O-specific polysaccharide from a marine bacterium Cellulophaga pacifica containing rarely occurredsugars, Fuc4NAc and ManNAcA

pp 69–72

Andrei V. Perepelov, Alexander S. Shashkov, Svetlana V. Tomshich*, Nadezhda A. Komandrova, Ol�ga I. Nedashkovskaya

α-D-Fucp4NAc1

4→3)-β-D-ManpNAcA-(1→4)-β-D-ManpNAcA-(1→3)-β-D-GlcpNAc-(1→

Contents / Carbohydrate Research 372 (2013) iii–vi v

The Roy L. Whistler International Award in Carbohydrate Chemistry 2014 p 78

Available online at www.sciencedirect.com

Abstracted/Indexed in: Chem. Abstr.: Curr. Contents: Phys., Chem. & Earth Sci. Life Sci. Current Awareness in Bio. Sci. (CABS).Science Citation Index. Full texts are incorporated in CJELSEVIER, a file in the Chemical Journals Online database whichis availabe on STN� International. Also covered in the abstract and citation database SciVerse Scopus�. Full text available onSciVerse ScienceDirect�

ISSN 0008-6215

*Corresponding authorSupplementary data available via SciVerse ScienceDirect

COVER

Multi-functionalisation of cyclodextrins (CD) has entered a new era thanks to the regioselective chemistry developed by M. Sollogoub’s group.As illustrated on the cover, many applications can now be reached using CDs with various functions on specific positions. An example offunctionalisation of CDs is given in the first issue of this journal. Image realised by Mickaël Ménand.

vi Contents / Carbohydrate Research 372 (2013) iii–vi