H

N-R
H
CH 2 OH Amino
OH H compound
H
H H C
OH
O
HO C
H O
H
Open chain D-glucose
 CH 2 OH
H OH H H+
H H C N-R
OH
HO C O H
-
H O
H
 CH 2 OH
H OH H H
H H C N-R
OH
HO C O
H H
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 OH H H
H H C N-R
OH
HO C O
H H
O Loss of water
H
 O
H H
CH 2 OH Water of
H OH H dehydration
H H C N-R
OH
HO C
H 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 OH H
H H C N-R
OH
HO C
H O
H
Open chain glycosylamine
 CH 2 OH
OH H H
H
H C N-R
OH
HO C
H O
H
Open chain glycosylamine
 CH 2 OH
OH H H
H
H C N-R
OH
HO C H
H
O

Open chain Amadori compound

• Attack by O-6 on the carbonyl group will
close the ring producing a 1-deoxy-1-
amino-D-fructopyranose compound (the
Amadori product)
 CH 2 OH
OH H H
H
H C N-R
OH
HO C H
H
O

Open chain Amadori compound

 H
H O OH
H H
H OH
HO N R
OH H
The Amadori compound
(a 1-deoxy-1-amino-D-fructopyranose)