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

2. Open chain D-glucose Amino compound

3. Open chain D-glucose

5. - +

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

8. Loss of water

9. Open chain glycosylamine Water of dehydration

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

11. Open chain glycosylamine

13. Open chain Amadori compound

14. Attack by O-6 on the carbonyl group will close the ring producing a 1-deoxy-1- amino-D-fructopyranose compound (the Amadori product)

15. Open chain Amadori compound

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