Carbohydrate Lecture

8/16/2019 Carbohydrate Lecture

1/20

An Introduction

W.T. Winter

[email protected]

215 Jahn Lab; x686

mailto:[email protected]:[email protected]


2/20

!"er"iew

# $onosaccharides%

# !&i'osaccharides%

# (o&ysaccharides# )&yco*roteins and (roteo'&ycans


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


4/20

,ext to &ast

carbondeter-ines

or L

,ew carbon is added as +1

/isher /or-u&as


5/20


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


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


8/20

:u'ars (reer To e +yc&ic


9/20

e-iaceta&s and +yc&i


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


11/20

(yranose >in' :ha*es

(yranose rin's can or- chair and boat

conor-ers

1+9 9+1


12/20

:ucrose

# 172 &inBed a&*ha

'&ucose= beta ructose

# :ources su'ar cane

su'ar beet


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


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


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


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


17/20

0xtrace&&u&ar $atrix4 ya&uronic acid

' regular copolymer of 2-acetyl glucosamine and Glucuronic 'cid $as a metal salt%


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


19/20

+onnecti"e Tissues7 ibrous

*roteins= *o&ysaccharides= and

*roteo'&cans


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.

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Carbohydrate Lecture