Reactions of

Monosaccharides

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1. Oxidation
1. Aldonic acid – oxidation of the carbonyl (aldehyde) carbon
2. Uronic acid – oxidation of the terminal CH2OH group
3. Aldaric acid – oxidation of both aldehyde and terminal CH2OH group

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2. Reduction
Alditol – can be prepared by the mild reduction (with NaBH4 or similar
agents) of the carbonyl groups of aldoses and ketoses.

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3. Chain Lengthening: The Kiliani–Fischer Synthesis

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4. Chain Shortening: The Wohl Degradation
• The Wohl degradation is the reverse of the Kiliani–Fischer synthesis
and involves the removal of a carbon atom from an aldose.

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5. Ruff Degradation

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6. Osazone formation

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What monosaccharide form the same osazone as D-
Ribose?

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7. Ester and Ether Formation

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8. Phosphorylation

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Glycoconjugates

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Glycoconjugates
Glycoconjugates are compounds which are formed by the covalent
linkage of carbohydrates to proteins and lipids.
1. Proteoglycans
2. Glycoprotein
3. Glycolipids

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1. Proteoglycans
- have extremely high carbohydrate content; occur on cell surfaces or
are secreted into the cellular matrix.
- are major components of connective tissue such as cartilage, in which
their many noncovalent interactions with other proteoglycans,
proteins, and glycosaminoglycans provide strength and resilience.

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2. Glycoprotein
- proteins that are covalently linked to carbohydrates via N- or O-
linkages; ubiquitous in most living organism.
- the oligosaccharide portions of glycoproteins are less monotonous
than the glycosaminoglycan chains of proteoglycans
- protection of polypeptide chains against proteolytic enzymes

N-Acetylgalactosamine 20
3. Glycolipids

Lipid and proteins on the cell membrane surface often have short
carbohydrate chains protruding out from the cell surface.
They form hydrogen bonds with the water molecules surrounding the
cell and thus help to stabilize membrane structure.

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