Page 46 - Color Atlas of Biochemistry

Carbohydrates 37

A. Reactions of the monosaccharides

Glucuronate Gluconolactone Sorbitol

6 COO HOCH 2 HOCH 2
H O OH H O H OH
H H H 1
OH H OH H O OH H CH OH
2
1
HO H HO HO
H OH H OH H OH

Oxidation Oxidation Reduction

HO CH 2 HO CH 2
H O OH β H O H
H H
OH H 1 Mutarotation OH H 1
HO H HO OH α
H OH H OH
β-D-Glucose α-D-Glucose

Esterification Epimerization Glycoside formation

O
6
O P O CH 2 H 1 HOCH 2 HOCH 2

O H O OH H O CH OH H O H H O H
2
H H H H
OH H H HO 2 OHHO OH H 1
HO H HO 3 OH HO 2 OH HO α O CH 3
H OH OH H H H H OH

Glucose 6- D-Fructose α-D-Mannose α-Methyl-
phosphate glucoside

B. Polarimetry, mutarotation
Polarizer Analyzer
α-D-Glucose: [ α ] = +112°
D
Water 100
˚
1. α ( )
a 80 62% β
Sugar
2. 60 + 52°
40 38% α
a
20
Sugar 0
3.
10 20 30 40 50 Time (min)
β-D-Glucose: [α] = +19°
D

Koolman, Color Atlas of Biochemistry, 2nd edition © 2005 Thieme
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