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CHAPTER 20
The Organic Chemistry of Carbohydrates
Important Terms
aldaric acid
the compound that results when the aldehyde and primary alcohol groups of an
aldose are oxidized to carboxylic acids.
alditol
the compound that results when the carbonyl group of an aldose is reduced to an
alcohol.
aldonic acid
the compound that results when the aldehyde group of an aldose is oxidized to a
carboxylic acid.
aldose
a polyhydroxy aldehyde.
amino sugar
a sugar in which one of the OH groups is replaced by an NH
2
group.
anomeric carbon
the carbon in a cyclic sugar that is the carbonyl carbon in the straight-chain form.
anomeric effect
preference for the axial position by substituents bonded to the anomeric carbon.
anomers
two cyclic sugars that differ in configuration only at the carbon that is the carbonyl
carbon in the straight-chain form.
bioorganic compound
an organic compound found in a living system.
carbohydrate
a sugar, a saccharide. Naturally occurring carbohydrates have the d-configuration.
complex carbohydrate
a carbohydrate that contains two or more sugar molecules linked together.
deoxy sugar
a sugar in which one of the OH groups has been replaced by a hydrogen.
disaccharide
a compound containing two sugar molecules linked together.
enediol rearrangement
a base-catalyzed reaction that interconverts monosaccharides.
epimerization
changing the configuration of a carbon by removing a proton and then
reprotonating it.
epimers
monosaccharides that differ in configuration at only one carbon.
furanose
a five-membered ring sugar.
furanoside
a five-membered ring glycoside.
glycoprotein
a protein that is covalently bonded to an oligosaccharide.
glycoside
the acetal of a sugar.