Amadori Rearrangement

Go to Slide Show mode and click the button to begin.

N-R

H
CH 2 OH
H

OH
H
OH

HO

O
H

Open chain D-glucose

H
O

Amino
compound

CH 2 OH
H

OH
H
OH

HO

O
H

Open chain D-glucose

H
O

N-R

CH 2 OH
H

OH
H
OH

HO

O
H

Open chain D-glucose

N-R

OH

CH 2 OH
H

H
OH

HO
H

OH H

H+

N-R

O
-

O
H

CH 2 OH
H

H
OH

HO
H

OH H

O
H

N-R

 This species is unstable and will lose water

to produce the open chain form of the
glycosylamine with a C-N double bond

CH 2 OH
H

H
OH

HO
H

OH H

O
H

N-R
Loss of water

O
H

CH 2 OH
H

H
OH

HO

Water of
dehydration

OH H

H
O
H

Open chain glycosylamine

N-R

 Rearrangement of this compound will yield

the Amadori compound. This sequence of
reactions is known as the Amadori
rearrangement.

CH 2 OH
H

H
OH

HO

OH H

O
H

Open chain glycosylamine

N-R

CH 2 OH
H

OH H

H
OH

HO

C
C

O
H

Open chain glycosylamine

N-R

CH 2 OH
H

H
OH

HO

C
C

OH H

N-R

Open chain Amadori compound

 Attack by O-6 on the carbonyl group will

close the ring producing a 1-deoxy-1amino-D-fructopyranose compound (the
Amadori product)

CH 2 OH
H

H
OH

HO

C
C

OH H

N-R

Open chain Amadori compound

H
H
H

O OH
OH

HO

H
N

OH

The Amadori compound

(a 1-deoxy-1-amino-D-fructopyranose)