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Chapter 25 Carbohydrates. 25.1 Classification of 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.

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classification of carbohydrates
Classification of Carbohydrates
  • monosaccharide
  • disaccharide
  • oligosaccharide
  • polysaccharide
monosaccharide
Monosaccharide
  • is not cleaved to a simpler carbohydrate on hydrolysis
  • glucose, for example, is a monosaccharide
disaccharide
Disaccharide
  • is cleaved to two monosaccharides on hydrolysis
    • these two monosaccharides may be the same or different

C12H22O11 + H2O

sucrose(a disaccharide)

disaccharide6
Disaccharide
  • is cleaved to two monosaccharides on hydrolysis
    • these two monosaccharides may be the same or different

C12H22O11 + H2O

C6H12O6 + C6H12O6

glucose(a monosaccharide)

sucrose(a disaccharide)

fructose(a monosaccharide)

higher saccharides
Higher Saccharides
  • oligosaccharide:
  • gives three or more monosaccharide units on hydrolysis
  • polysaccharide:
  • yields more than 10 monosaccharide units
table 25 1 some classes of carbohydrates
Table 25.1 Some Classes of Carbohydrates
  • No. of carbons AldoseKetose
  • 4 AldotetroseKetotetrose
  • 5 AldopentoseKetopentose
  • 6 AldohexoseKetopentose
  • 7 AldoheptoseKetoheptose
  • 8 AldooctoseKetooctose
enantiomers of glyceraldehyde

CH

O

CH

O

H

OH

HO

H

D

L

CH2OH

CH2OH

Enantiomers of Glyceraldehyde

(+)-Glyceraldehyde

(–)-Glyceraldehyde

an aldotetrose

CH

O

H

OH

H

OH

CH2OH

An Aldotetrose

1

  • stereochemistry assigned on basis of whetherconfiguration of highest-numbered stereogenic centeris analogous to D or L-glyceraldehyde

2

3

4

an aldotetrose17

CH

O

H

OH

H

OH

CH2OH

An Aldotetrose

1

  • stereochemistry assigned on basis of whetherconfiguration of highest-numbered stereogenic centeris analogous to D or L-glyceraldehyde

2

3

D

4

an aldotetrose18

CH

O

H

OH

H

OH

CH2OH

An Aldotetrose

1

2

3

4

D-Erythrose

the four aldotetroses

CH

O

CH

O

H

OH

HO

H

H

OH

HO

H

CH2OH

CH2OH

The Four Aldotetroses
  • D-Erythrose and L-erythrose are enantiomers

D-Erythrose

L-Erythrose

the four aldotetroses20

CH

O

CH

O

H

OH

H

HO

H

OH

H

OH

CH2OH

CH2OH

The Four Aldotetroses
  • D-Erythrose and D-threose are diastereomers

D-Erythrose

D-Threose

the four aldotetroses21

CH

O

CH

O

HO

H

H

HO

HO

H

H

OH

CH2OH

CH2OH

The Four Aldotetroses
  • L-Erythrose and D-threose are diastereomers

L-Erythrose

D-Threose

the four aldotetroses22

CH

O

CH

O

H

OH

H

HO

H

HO

H

OH

CH2OH

CH2OH

The Four Aldotetroses
  • D-Threose and L-threose are enantiomers

L-Threose

D-Threose

the four aldotetroses23

CH

O

CH

O

CH

O

CH

O

H

OH

HO

H

OH

H

HO

H

H

OH

H

OH

HO

HO

H

CH2OH

CH2OH

CH2OH

CH2OH

The Four Aldotetroses

H

D-Erythrose

L-Erythrose

D-Threose

L-Threose

the aldopentoses
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

OH

OH

OH

OH

H

H

H

CH2OH

CH2OH

CH2OH

CH2OH

The Four D-Aldopentoses

H

D-Ribose

D-Arabinose

D-Xylose

D-Lyxose

the four d aldopentoses27

CH

O

CH

O

CH

O

CH

O

OH

OH

HO

H

H

HO

H

H

OH

OH

OH

OH

H

H

H

CH2OH

CH2OH

CH2OH

CH2OH

The Four D-Aldopentoses

H

D-Ribose

D-Arabinose

D-Xylose

D-Lyxose

the four d aldopentoses28

CH

O

CH

O

CH

O

CH

O

OH

HO

H

OH

HO

H

H

H

OH

OH

HO

H

H

HO

H

H

OH

OH

OH

OH

H

H

H

H

CH2OH

CH2OH

CH2OH

CH2OH

The Four D-Aldopentoses

D-Ribose

D-Arabinose

D-Xylose

D-Lyxose

the four d aldopentoses29

CH

O

CH

O

CH

O

CH

O

OH

HO

H

OH

HO

H

H

H

OH

OH

HO

H

H

HO

H

H

OH

OH

OH

OH

H

H

H

H

CH2OH

CH2OH

CH2OH

CH2OH

The Four D-Aldopentoses

D-Ribose

D-Arabinose

D-Xylose

D-Lyxose

aldohexoses
Aldohexoses
  • There are 16 aldopentoses.
  • 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 described in Section 25.5.