Carbohydrates
H C OH C O
HO C H HO C H
H C OH H C OH
H C OH H C OH
CH2OH CH2OH
D-glucose D-fructose
D vs L Designation
CHO CHO
D & L designations
H C OH HO C H
are based on the
configuration about CH2OH CH2OH
the single asymmetric D-glyceraldehyde L-glyceraldehyde
C in glyceraldehyde.
CHO CHO
The lower H C OH HO C H
representations are
CH2OH CH2OH
Fischer Projections.
D-glyceraldehyde L-glyceraldehyde
Sugar Nomenclature
H H
An aldehyde can
C O + R' OH R' O C OH
react with an
alcohol to form R R
a hemiacetal. aldehyde alcohol hemiacetal
R R
A ketone can
react with an C O + "R OH "R O C OH
alcohol to form R' R'
a hemiketal. ketone alcohol hemiketal
1
CHO
Pentoses and
H C OH
hexoses can cyclize 2
HO C H
as the ketone or 3 D-glucose
aldehyde reacts H C OH (linear form)
4
with a distal OH. H
5
C OH
Glucose forms an 6
CH2OH
intra-molecular 6 CH2OH 6 CH2OH
hemiacetal, as the 5 5
H O H H O OH
C1 aldehyde & H H
4 1 4 1
C5 OH react, to OH H OH H
form a 6-member OH
3 2
OH OH
3 2
H
pyranose ring, H OH H OH
named after pyran. -D-glucose -D-glucose
-D-glucopyranose -D -glucopyranose
H O H H O H
H H
OH H OH H
OH OH OH O OH
H NH 2 H N C CH 3
H
-D-glucosamine -D-N-acetylglucosamine
H3C C NH O COO
R HC OH
H H R=
HC OH
H OH
CH2OH
OH H
N-acetylneuraminate (sialic acid)
H OH H OH
H O H2O H O
HO HO
HO H + CH 3 -O H HO H
H OH H OH
H OH H O CH 3
-D-glucopyranose methanol methyl--D-glucopyranose
6 CH 2 O H 6 CH 2 O H
Disaccharides: H
5 O H H
5 O H
H H
Maltose, a cleavage 4 OH H 1 4
OH H 1
product of starch OH 3 2
O
3 2
OH
disaccharide with an
(1 4) glycosidic 6 CH 2 O H 6 CH
2O H
5 O 5 O
link between C1 - C4 H
H
H
H
OH
OH of 2 glucoses. 4
OH H 1 O 4
OH H 1
H H
It is the anomer OH 3 2 3 2
H OH
(C1 O points down). cellobiose
H OH
Polysaccharides:
Plants store glucose as amylose or amylopectin, glucose
polymers collectively called starch.
Glucose storage in polymeric form minimizes osmotic
effects.
Amylose is a glucose polymer with (14) linkages.
The end of the polysaccharide with an anomeric C1 not
involved in a glycosidic bond is called the reducing end.
CH 2OH CH 2OH
H O H H O H amylopectin
H H
OH H OH H 1
O
OH
O
H OH H OH
CH 2 OH CH 2 OH 6 CH 2 CH 2 OH CH 2 OH
H O H H O H H 5 O H H O H H O H
H H H H H
OH H OH H OH H 1 4 OH H OH H
4 O O
O O OH
OH
3 2
H OH H OH H OH H OH H OH
transmembrane
-helix
cytosol
CH 2 O H
D -glucuronate 6
H 5 O
Websites on: 6 COO H
1 O
4 H
H O
Aggrecan H
5
OH H
4 H 1 3 2
OH
Aggrecan & v H O
H NH COCH 3
2
ersican H
3
OH N -acetyl- D -glucosam ine
.
hyaluronate
iduronate-2-sulfate N-sulfo-glucosamine-6-sulfate
H CH2OSO3
H O H O H
COO H
OH H O OH H
H O
H OSO3 H NHSO3
heparin or heparan sulfate - examples of residues
H O HN C CH2 CH Asn
H
H C O
OH
H HN
OH
HC R X
H HN C CH3
C O
O
N-acetylglucosamine HN