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8/16/2019 Carbohydrate Lecture
1/20
An Introduction
W.T. Winter
215 Jahn Lab; x686
8/16/2019 Carbohydrate Lecture
2/20
!"er"iew
# $onosaccharides%
# !&i'osaccharides%
# (o&ysaccharides# )&yco*roteins and (roteo'&ycans
8/16/2019 Carbohydrate Lecture
3/20
+arbohydrates Are +hira&
$o&ecu&es
D
L
Glyceraldehyde
Typically but not always
# L – amino acids
# D - sugars
Hence, these molecules havea measurable optical
rotation, which depends
upon both the monomer
residues and their
conformation
8/16/2019 Carbohydrate Lecture
4/20
,ext to &ast
carbondeter-ines
or L
,ew carbon is added as +1
/isher /or-u&as
8/16/2019 Carbohydrate Lecture
5/20
8/16/2019 Carbohydrate Lecture
6/20
A Way to 0x*&ore $onosaccharides
# John $aser at Leeds has de"e&o*ed a
$onosaccharide rowser3 the site is
htt*4www.beechtreeco--on.or'bioche-
istry-onosaccharide
http://www.beechtreecommon.org/biochemistry/monosaccharidehttp://www.beechtreecommon.org/biochemistry/monosaccharidehttp://www.beechtreecommon.org/biochemistry/monosaccharidehttp://www.beechtreecommon.org/biochemistry/monosaccharide
8/16/2019 Carbohydrate Lecture
7/20
0*i-ers ier by +oni'uration at
!ne +hira& +enter
7'&ucose +2 e*i-er 7-annose
+ e*i-er 7a&&ose
+9 e*i-er 7'a&actose
+5 e*i-er L7idose
8/16/2019 Carbohydrate Lecture
8/20
:u'ars (reer To e +yc&ic
8/16/2019 Carbohydrate Lecture
9/20
e-iaceta&s and +yc&i
8/16/2019 Carbohydrate Lecture
10/20
β77)&ucose
# In nature= o*en chain
or-s are rare.
# ,$> has shown that
a&& 5 coexist with the*yranose or-s
occurrin' ?? o the
ti-e= uranose about
.5 each and a
trace o o*en chain
α and β are ano-ersand dier in
coni'uration at thenew chira& center
or-ed in the cyc&e
8/16/2019 Carbohydrate Lecture
11/20
(yranose >in' :ha*es
(yranose rin's can or- chair and boat
conor-ers
1+9 9+1
8/16/2019 Carbohydrate Lecture
12/20
:ucrose
# 172 &inBed a&*ha
'&ucose= beta ructose
# :ources su'ar cane
su'ar beet
8/16/2019 Carbohydrate Lecture
13/20
(o&ysaccharides
# (o&ysaccharides consist o su'ar residues&inBed into a *o&y-er.
# (o&ysaccharides= un&iBe *roteins or nuc&eic
acids= are not a&ways &inear in seCuence# The -ost abundant bio-o&ecu&es in
nature7about 112 tons o ce&&u&ose are
synthesi
8/16/2019 Carbohydrate Lecture
14/20
(o&ysaccharides $ay e the $ost
i"erse io-o&ecu&es
/ro- one 6 carbonhexo*yranose su'arsuch as '&ucose= youcan -aBe 11 dierentdisaccharides and 8o those &ead toininite *o&y-ers
/ro- one a-ino acid ornuc&eotide you can-aBe on&y a sin'&edi-er.
o
CH!H
!H
!H
!H
!H
o
CH!H
!H
!H
!H
!H
-D-Glucose -D-Glucose
8/16/2019 Carbohydrate Lecture
15/20
+e&&u&ose4 :tructura&
*o&ysaccharide ro- '&ucose
"icrofibrils
of cellulose #ood cell $fiber% cell walls
are made of cellulose &lignin and hemicelluloses
'lso found in some
bacteria, algae, fungi,
seed hairs, and
animals $tunicates or
sea s(uirts%
n ) *+++-++++
:t h )& & d
8/16/2019 Carbohydrate Lecture
16/20
:tarch4 a77)&ucose *o&y-er ound
as an ener'y stora'e -ateria& in
oods
'mylopectin
'mylose
nli.e cellulose,
starch can be
metaboli/ed by
humans0
1tarches providethe bul. of the
energy we obtain
from grains,
potatoes etc0
8/16/2019 Carbohydrate Lecture
17/20
0xtrace&&u&ar $atrix4 ya&uronic acid
' regular copolymer of 2-acetyl glucosamine and Glucuronic 'cid $as a metal salt%
8/16/2019 Carbohydrate Lecture
18/20
A cont
/ound in4
# syno"ia& &uid DBnee= shou&der E
# Fitreous hu-or Deye7 used inreconstructi"e eye sur'eryE
# :Bin G s-a&& a-ounts in a&& connecti"e
tissues
+ ti Ti ib
8/16/2019 Carbohydrate Lecture
19/20
+onnecti"e Tissues7 ibrous
*roteins= *o&ysaccharides= and
*roteo'&cans
8/16/2019 Carbohydrate Lecture
20/20
!ther :tructura& (o&ysaccharides
# $annans G so-e a&'ae
# A&'inic acids G -any a&'ae
# +hitin7 insects= crustaceans Dshri-* she&&E=un'i.