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Carbohydrates
Carbohydrates (glycans) have the following
basic composition: I
(CH2O)n or H - C - OH
I
Monosaccharides - simple sugars with multiple OH
groups. Based on number of carbons (3, 4, 5, 6), a
monosaccharide is a triose, tetrose, pentose or hexose.
Disaccharides - 2 monosaccharides covalently linked.
Oligosaccharides - a few monosaccharides covalently
linked.
Polysaccharides - polymers consisting of chains of
monosaccharide or disaccharide units.
Monosaccharides
Aldoses (e.g., glucose) have Ketoses (e.g., fructose) have
an aldehyde group at one end. a keto group, usually at C2.
H O
C CH2OH
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
The two families of monosaccharides are aldoses and ketoses
Representative
monosaccharides
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
Glucose and other sugars capable of reducing Cu 2+ are called reducing sugars
CHO
Pentoses and 1
H C OH
hexoses can cyclize 2
as the ketone or HO
3
C H D-glucose
aldehyde reacts H C OH (linear form)
4
with a distal OH. H C OH
5
Glucose forms an 6
CH2OH
intra-molecular 6 CH2OH 6 CH2OH
hemiacetal, as the 5 5
O O
C1 aldehyde & H
H
H H
H
OH
C5 OH react, to 4 OH H 1 4 OH H 1
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
2C O
HO C H
1 CH2OH
3 HOH2C 6 O
H C OH
4 5 H HO 2
H C OH H 4 3 OH
5
OH H
6
CH2OH
C OH H
CHO
C OH
oxidized to a HO
H
C
C
H
OH
HO
H
C
C OH
H
carboxylic acid; H C OH
CH 2OH
H C
COOH
OH
glucuronic acid.
Sugar derivatives
CH 2OH CH 2OH
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 H 2O 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
Disaccharides contain a glycosidic bond
anomeric carbon
Formation
of
maltose
Glu(1→4)Glu
Some common disaccharides
configuration of
the anomeric carbons joined by
The glycosidic bond
Carbon
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
H H
It is the anomer OH 3 2 3 2
Most carbohydrates
und in nature occur
s polysaccharides.
Some homopolysaccharides are stored forms of fuel
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 2 OH CH 2 OH
H O H H O H amylopectin
H H
OH H OH H 1
O
OH
O
H OH H OH
CH 2OH CH 2 OH 6 CH 2 CH 2 OH CH 2OH
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 2
3
H OH H OH H OH H OH H OH
occurs every
24 to 30 residues
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
June beetle
(exoskeleton of chitin)
Bacterial and algal cell walls contain structural heteropolysaccharides
Peptidoglycan
(alternating 1→4-linked GlcNac-Mur2Ac crosslinked by short peptides)
Glucoronic acid
N-Acetylglucosamine
Connective Tissues and
Polysaccharides
• Blood vessels, cartilages and tendons
• Contain protein fibers embedded in a syrupy
matrix containing unbranched
polysaccharides (mucopolysaccharides)
• Tendons- gel-like mixture of polysaccharides
with water serve as lubricants and shock
absorbers around joints and in extracellular
spaces.
Chondroitin 6-sulfate
• Tendons and cartilages
• Linked to protein
• Has been used in artificial skin
• With glucuronic acid and glucosamine
sulfate- dietary supplements- promoted as
cure for osteoarthritis (due to deterioration
of cartilage at joints)
CH 2 O H
D -glucuronate 6
H 5 O
6 COO
H
4 1 O
O H
H 5
H OH H
4 H 1 3 2
OH
H H NH COCH 3
3 2 O
H OH N -acetyl- D -glucosam ine
hyaluronate
Glycosaminoglycans (mucopolysaccharides) are linear polymers of
repeating disaccharides (Slime-like consistency)
The constituent monosaccharides tend to be modified, with acidic
groups, amino groups, sulfated hydroxyl and amino groups, etc.
-acidic heteropolysaccharides (highly hydrated, gel-like sticky
material due to the negative charge)
-proteoglycans (properties are due more to the CHO than the
protein
Major types of acidic
heteropolysaccharides
• Hyaluronic acid
• Chondroitin 4-sulfate
• Chondroitin 6-sulfate
• Dermatan sulfate
• Heparin
• Heparan sulfate
• Possess similar repeating disaccharide (glucuronic
acid, N-acetyl-D-glucosamine, D-galactose, etc.)
CH 2 O H
D -g lu cu ro n ate 6
H 5 O
6 COO H
4 1 O
O H
H 5
H OH H
4 H 1 3 2
OH
H H NH COCH 3
3 2 O
H OH N -acetyl- D -g lu co sam in e
hyaluronate
Hyaluronate (hyaluronan) - a glycosaminoglycan with a repeating
disaccharide consisting of 2 glucose derivatives, glucuronate
(glucuronic acid) & N-acetyl-glucosamine.
-synovial fluid- lubricates joints and found in eyes.
•Biological cement filling the intercellular spaces
•A gel-like network acting as a biological filter retaining
microbiotic and other large molecules invading the organisms
The glycosidic linkages are (13) & (14).
• Dermatan sulfate- found in the aorta and
possess anticoagulant property
• Keratan sulfate- cornea and bound to a
protein
heparan sulfate
core glycosaminoglycan
protein
transmembrane
-helix
cytosol
CH 2 O H
D -glucuronate 6
H 5 O
Websites on: 6 COO
H
4 1 O
O H
H
Aggrecan H
5
OH H
4 H 1 3 2
OH
Aggrecan & H H NH COCH 3
O
versican. 3 2
H 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
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 serine
that are covalently OH H
NH
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
Proteoglycan structure
Two families of membrane proteoglycans
Cross-linked meshwork
that gives the whole
extracellular matrix strength
and resilience
Glycoproteins have covalently attached oligosaccharides
Principal determinant
of the serotype
(immunological reactivity)
of the bacterium
Helicobacter pylori
cells adhering to the
gastric surface
Galactose