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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
react with an
C O + R' OH R' O C OH
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 O 5 O
H H H OH
C1 aldehyde & H H
4 H 1 4 H 1
C5 OH react, to OH OH
OH OH OH H
form a 6-member 3 2 3 2
pyranose ring, H OH H OH
2C O
HO C H
1 CH2OH
3 HOH2C 6 O
H C OH HO
4 5 H 2
H C OH H 4 3 OH
5
OH H
6
CH2OH
-D-glucopyranose -D-glucopyranose
H O H H O H
H H
OH H OH H
OH OH OH O OH
H NH2 H N C CH3
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 + CH3-OH HO H
H OH H OH
H OH H OCH3
-D-glucopyranose methanol methyl--D-glucopyranose
6 CH2OH 6 CH2OH
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
(e.g., amylose), is a H OH
maltose H OH
disaccharide with an
(1 4) glycosidic 6 CH2OH
5
6 CH2OH
O 5 O OH
link between C1 - C4 H
H
H
H
OH of 2 glucoses. 4
OH H 1 O 4
OH H 1
H
It is the anomer OH H
3 2 3 2
H OH H OH
(C1 O points down). cellobiose
Cellobiose, a product of cellulose breakdown, is the
otherwise equivalent anomer (O on C1 points up).
The (1 4) glycosidic linkage is represented as a zig-zag,
but one glucose is actually flipped over relative to the other.
Other disaccharides include:
Sucrose, common table sugar, has a glycosidic bond
linking the anomeric hydroxyls of glucose & fructose.
Because the configuration at the anomeric C of glucose
is (O points down from ring), the linkage is (12).
The full name of sucrose is -D-glucopyranosyl-(12)-
-D-fructopyranose.)
Lactose, milk sugar, is composed of galactose &
glucose, with (14) linkage from the anomeric OH of
galactose. Its full name is -D-galactopyranosyl-(1 4)-
-D-glucopyranose
CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O H O H O H H O H
H H H H H
H H H H H
OH H 1 4 OH H 1 OH H OH H OH H
O O O O OH
OH 2
3
H OH H OH H OH H OH H OH
amylose
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.
CH2OH CH2OH
H O H H O H amylopectin
H H
OH H OH H 1
O
OH
O
H OH H OH
transmembrane
-helix
cytosol
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
OH H O OH H
Diagram H O
by Kirkpatrick
H OSO3 H NHSO3
& Selleck.
heparin or heparan sulfate - examples of residues
CH2OH C O
Oligosaccharides H O O CH2 CH
H NH serine
that are covalently OH H residue
attached to proteins OH O H
or to membrane H HN C CH3
lipids may be linear
-D-N-acetylglucosamine
or branched chains.
H O O CH2 CH
H NH serine
OH H residue
OH O H
H HN C CH3
-D-N-acetylglucosamine
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
Man Key:
NAN = N-acetylneuraminate
NAG Gal = galactose
NAG = N-acetylglucosamine
NAG Fuc
Man = mannose
Fuc = fucose
Asn