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Monosaccharide Nomenclature
Classification based on location of the double bond C=O
The family-name ending -ose indicates a carbohydrate
Monosaccharide Classification
using # of C atoms in the chain
adapted from
ull.chemistry.uakron.edu
The D and L classification is from optical activity
Physical Properties
Optical Activity
Ability to rotate planar polarized light
the α form has the -OH on the opposite side from the -CH2OH (below the plane of the ring)
the β form has the -OH on the same side as the -CH2OH (above the plane of the ring)
Haworth Projections
Monosaccharide: Fructose
A ketohexose, can also form a 5-membered ring in solution
Monosaccharide: Ribose
Reactions of Monosaccharide
Phosphate esters
The –OH groups of sugars can add phosphate groups to form phosphate esters.
Disaccharides
1,4-Glycosidic Links
Polysaccharides
Branched Polysaccharides
In Summary
Monosaccharides are simple sugars
Cyclic sugars: Cyclization by internal hemiacetal formation. Forms between C1 and C5.
Anomers: α and β anomers from Haworth (ring) structures. In the α form the –OH on C1
is on the opposite of –CH2OH (C6).
In the β form they are on the same side of the ring.
A reducing sugar: A carbohydrate that gets oxidized itself to carboxylic acid. It reduces
the oxidizing agent used. (Generally aldoses are reducing sugars).
1. aldotriose
2. aldopentose
3. ketotriose
4. ketopentose
What is the maximum number of aldotetrose
stereoisomers?
1. One
2. Two
3. Three
4. Four
1. α-D-galactose
2. α-L-galactose
3. β-D-galactose
4. β -L-galactose
The cyclic structure below is
1. α-D-galactose
2. α-L-galactose
3. β-D-galactose
4. β -L-galactose
1. Cysteine
2. Glutamine
3. Threonine
4. Tyrosine