Carbohydrates

Classification of Carbohydrates

monosaccharide disaccharide oligosaccharide polysaccharide

Monosaccharide

is not cleaved to a simpler carbohydrate on hydrolysis

glucose, for example, is a monosaccharide

Disaccharide is cleaved to two monosaccharides on hydrolysis these two monosaccharides may be the same or different C12H22O11 + H2O

sucrose (a disaccharide)

Disaccharide is cleaved to two monosaccharides on hydrolysis these two monosaccharides may be the same or different C12H22O11 + H2O C6H12O6 + C6H12O6

sucrose (a disaccharide)

glucose (a monosaccharide)

fructose (a monosaccharide)

Higher Saccharides oligosaccharide: gives three or more monosaccharide units on hydrolysis polysaccharide: yields more than 10 monosaccharide units

Table 1 Some Classes of Carbohydrates

No. of carbons
4

Aldose
Aldotetrose

Ketose
Ketotetrose

5 6 7
8

Aldopentose Aldohexose Aldoheptose

Aldooctose

Ketopentose Ketohexose Ketoheptose

Ketooctose

Fischer Projections and D-L Notation

Fischer Projections

Fischer Projections

Fischer Projections of Enantiomers

Fischer Projections of Enantiomers

Enantiomers of Glyceraldehyde

CH H

O OH HO

CH

O H

CH2OH (+)-Glyceraldehyde

CH2OH ()-Glyceraldehyde

The Aldotetroses

An Aldotetrose
1

CH

O OH
OH

H
H

CH2OH

stereochemistry assigned on basis of whether configuration of highest-numbered stereogenic center is analogous to D or L-glyceraldehyde

An Aldotetrose
1

CH

O OH
OH

H
H

CH2OH

stereochemistry assigned on basis of whether configuration of highest-numbered stereogenic center is analogous to D or L-glyceraldehyde

An Aldotetrose
1

CH

O OH
OH

H
H

CH2OH

D-Erythrose

The Four Aldotetroses

CH H
H

O OH
OH

CH HO HO H
H

O
D-Erythrose and L-erythrose are

enantiomers

CH2OH
D-Erythrose

CH2OH
L-Erythrose

The Four Aldotetroses

CH H
H

O OH
OH

CH HO
H

O H
OH
D-Erythrose and D-threose are

diastereomers

CH2OH
D-Erythrose

CH2OH
D-Threose

The Four Aldotetroses

CH HO HO H
H

O HO
H

CH H

O
L-Erythrose and D-threose are

diastereomers
OH CH2OH
D-Threose

CH2OH
L-Erythrose

The Four Aldotetroses

CH
D-Threose and L-threose are

O H
OH

CH H
HO

O OH H

HO
H

enantiomers

CH2OH
D-Threose

CH2OH
L-Threose

The Four Aldotetroses

CH H
H

O OH HO
OH HO

CH H
H

O HO
H

CH H

O H

CH

O OH H

OHHO CH2OH

CH2OH
D-Erythrose

CH2OH
L-Erythrose

CH2OH
L-Threose

D-Threose

Aldopentoses and Aldohexoses

The Aldopentoses

There are 8 aldopentoses. Four belong to the D-series; four belong to the L-series.
Their names are ribose, arabinose, xylose, and lyxose.

The Four D-Aldopentoses

CH

CH

CH

CH

OH

OH

OH

OH

CH2OH
D-Ribose

CH2OH
D-Arabinose

CH2OH
D-Xylose

CH2OH
D-Lyxose

The Four D-Aldopentoses

CH

CH

CH

CH

H H

OH
OH

H H

OH HO
OH

H
OH

HO H

H
OH

CH2OH
D-Ribose

CH2OH
D-Arabinose

CH2OH
D-Xylose

CH2OH
D-Lyxose

The Four D-Aldopentoses

CH

CH

CH

CH

H H H

OH HO OH
OH

H
OH

H H

OH HO H
OH

H H
OH

H H

OH HO

HO H

CH2OH
D-Ribose

CH2OH
D-Arabinose

CH2OH
D-Xylose

CH2OH
D-Lyxose

The Four D-Aldopentoses

CH

CH

CH

CH

H H H

OH HO OH
OH

H
OH

H H

OH HO H
OH

H H
OH

H H

OH HO

HO H

CH2OH
D-Ribose

CH2OH
D-Arabinose

CH2OH
D-Xylose

CH2OH
D-Lyxose

Aldohexoses

There are 16 aldohexoses. 8 belong to the D-series; 8 belong to the Lseries.

Their names and configurations are best remembered with the aid of the mnemonic.