Carbohydrates

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• Carbohydrates are the most abundant biomolecules on
Earth.
• Many, but not all, carbohydrates have the empirical
formula (CH2O)n; some also contain nitrogen,
phosphorus, or sulfur.

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Roles of Carbohydrates
1. Energy storage
2. Metabolic intermediate
3. Structural framework of RNA and DNA

4. Structure and protection of plants

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Structure of Carbohydrates
Carbohydrates can be drawn using
1. Fischer projection 2. Haworth projection 3. Chair conformation

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Seatwork
Consider the structure of D-Galactose. Draw its haworth and chair
conformation.

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Isomerism in Carbohydrates
1. Aldose-ketose isomerism

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2. Enantiomers (D vs. L)

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3. Epimers
Diastereomers of carbohydrates which differ only in the
orientation of one carbon.

D-Mannose is a C2 epimer
of D-Glucose

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4. Pyranose and furanose ring structures
• Furanose - 5-membered ring structure
• Pyranose – 6-membered ring structure

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5. α and β- anomers
α-anomer – the -OH at C1 is trans to the C6 group
β-anomer – the -OH at C1 is cis to the C6 group

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Three major size classes of carbohydrates
1. Monosaccharides
2. Oligosaccharides
3. Polysaccharides
(the word “saccharide” is derived from the Greek sakcharon, meaning
“sugar”).

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1. Monosaccharides
• Simple sugars
• The most abundant monosaccharide in nature is the six-carbon sugar
D-glucose, sometimes referred to as dextrose

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The Two Families of Monosaccharides Are
Aldoses and Ketoses
• If the carbonyl group is at an • If the carbonyl group is at any
end of the carbon chain (that is, other position (in a ketone
in an aldehyde group) the group) the monosaccharide is
monosaccharide is an aldose. a ketose.

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D-Aldoses

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D-Ketoses

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2. Oligosaccharides
• Consist of short chains of monosaccharide units, or residues, joined by
characteristic linkages called glycosidic bonds.
• The most abundant are the disaccharides, with two monosaccharide
units.
• Disaccharides contain a glycosidic bond
• O-glycosidic bond formed when a hydroxyl group of one sugar reacts
with the anomeric carbon of the other

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Disaccharides

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In describing disaccharides or polysaccharides, the end of a chain with a free anomeric
carbon (one not involved in a glycosidic bond) is commonly called the reducing end.

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3. Polysaccharides
• Sugar polymers containing more than 20 or so monosaccharide units,
and some have hundreds or thousands of units.
• Polysaccharides, also called glycans, differ from each other in the
identity of their recurring monosaccharide units, in the length of their
chains, in the types of bonds linking the units, and in the degree of
branching.
• Homopolysaccharides contain only a single type of monomer
Ex. starch and glycogen
cellulose and chitin
• Heteropolysaccharides contain two or more different kinds

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Polysaccharide
1. Starch – energy reservoir of plant cells; made up of two
polysaccharides (amylose and amylopectin).
o Amylose – long, unbranched chains of D-glucose residues connected
by α(1->4) linkages.

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o Amylopectin – branched polymer
– glycosidic linkages joining successive glucose residues
in amylopectin chains are α(1->4); the branch points (occurring every
24 to 30 residues) are α(1->6) linkages.

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Starch

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2. Glycogen – main storage polysaccharide of animal cells.
– polymer of α(1->4)-linked subunits of glucose, with α(1->6)-
linked branches
– extensively branched (on average, every 8 to 12 residues)
and compact
Glycogen phosphorylase – cleaves one glucose at a time from the
nonreducing end of a branch to produce glucose-1-phosphate, which then
enters the metabolic pathways of carbohydrate breakdown.

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3. Cellulose – fibrous, tough, water-insoluble substance, found in the
cell walls of plants

– linear, unbranched homopolysaccharide, consisting of 10,000 to

15,000 D-glucose units
– glucose residues are linked by β(1->4) glycosidic bonds

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4. Chitin – linear homopolysaccharide with all the residues linked in
β(1->4) glycosidic bonds.
– similar to cellulose in both structure and function
– the monomer is N-acetyl-β-D-glucosamine

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