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

glucose
sucrose (a monosaccharide)
fructose
(a disaccharide)
(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 Aldose Ketose

4 Aldotetrose Ketotetrose
5 Aldopentose Ketopentose
6 Aldohexose Ketohexose
7 Aldoheptose Ketoheptose
8 Aldooctose Ketooctose
Fischer Projections and D-L Notation
Fischer Projections
Fischer Projections
Fischer Projections of Enantiomers
Fischer Projections of Enantiomers
 Enantiomers of Glyceraldehyde

CH O CH O

H OH HO H
D L

CH2OH CH2OH

(+)-Glyceraldehyde (–)-Glyceraldehyde
The Aldotetroses
 An Aldotetrose

1 CH O
2
H OH
3
H OH

4
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
2
H OH
3
H OH
D 4
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
2
H OH
3
H OH

4
CH2OH

D-Erythrose
 The Four Aldotetroses

CH O CH O

H OH HO H D-Erythrose and
L-erythrose are
H OH HO H enantiomers

CH2OH CH2OH

D-Erythrose L-Erythrose
 The Four Aldotetroses

CH O CH O
D-Erythrose and
H OH HO H D-threose are
diastereomers
H OH H OH

CH2OH CH2OH

D-Erythrose D-Threose
 The Four Aldotetroses

CH O CH O
L-Erythrose and
HO H HO H D-threose are
diastereomers
HO H H OH

CH2OH CH2OH

L-Erythrose D-Threose
 The Four Aldotetroses

CH O CH O
D-Threose and
HO H H OH
L-threose are
enantiomers
H OH HO H

CH2OH CH2OH

D-Threose L-Threose
 The Four Aldotetroses

CH O CH O CH O CH O

H OH HO H HO H H OH

H OH HO H H OHHO H

CH2OH CH2OH CH2OH CH2OH

D-Erythrose L-Erythrose D-Threose L-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 O CH O CH O CH O

H OH H OH H OH H OH

CH2OH CH2OH CH2OH CH2OH

D-Ribose D-Arabinose D-Xylose D-Lyxose

 The Four D-Aldopentoses

CH O CH O CH O CH O

H OH H OH HO H HO H
H OH H OH H OH H OH

CH2OH CH2OH CH2OH CH2OH

D-Ribose D-Arabinose D-Xylose D-Lyxose

 The Four D-Aldopentoses

CH O CH O CH O CH O

H OH HO H H OH HO H
H OH H OH HO H HO H
H OH H OH H OH H OH

CH2OH CH2OH CH2OH CH2OH

D-Ribose D-Arabinose D-Xylose D-Lyxose

 The Four D-Aldopentoses

CH O CH O CH O CH O

H OH HO H H OH HO H
H OH H OH HO H HO H
H OH H OH H OH H OH

CH2OH CH2OH CH2OH CH2OH

D-Ribose D-Arabinose D-Xylose D-Lyxose

 Aldohexoses

There are 16 aldohexoses.

8 belong to the D-series; 8 belong to the L-
series.
Their names and configurations are best
remembered with the aid of the mnemonic.