Amadori Rearrangement

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Presentation transcript:

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

Amino compound Open chain D-glucose

Open chain D-glucose

Open chain D-glucose

+ -

This species is unstable and will lose water to produce the open chain form of the glycosylamine with a C-N double bond

Loss of water

Water of dehydration Open chain glycosylamine

Rearrangement of this compound will yield the Amadori compound Rearrangement of this compound will yield the Amadori compound. This sequence of reactions is known as the Amadori rearrangement.

Open chain glycosylamine

Open chain glycosylamine

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)

Open chain Amadori compound

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