Amadori Rearrangement

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N-R
H
CH 2 OH H H OH HO H OH H O
Amino compound

H
C

O H

Open chain D-glucose

H
CH 2 OH H H OH HO H OH H O

N-R
H
C

H
C

O H

Open chain D-glucose

CH 2 OH H H OH HO H OH H

H
C

N-R
OH

O H

Open chain D-glucose

CH 2 OH H H OH HO H OH H

H+

H
C

C O -

N-R
H

O H

CH 2 OH H H OH HO H OH H

H
C

C O

N-R

O H

 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

H
C

C O

N-R

O H

H
Loss of water

O H H

CH 2 OH H H OH HO H OH H

Water of dehydration

H
C

N-R

O H

Open chain glycosylamine

 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 H OH H

H
C

N-R

O H

Open chain glycosylamine

CH 2 OH H H OH HO H C OH H C

N-R

O H

Open chain glycosylamine

CH 2 OH H H OH HO H C OH H C

N-R

O
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 H C OH H C

N-R

O
Open chain Amadori compound

H H H HO OH H H O OH H OH N R

The Amadori compound (a 1-deoxy-1-amino-D-fructopyranose)