DEUTERIUM INCORPORATION DURING CONVERSION OF 1-AMINO-1-DEOXY-D-FRUCTOSE DERIVATIVES TO 5-(HYDROXYMETHYL)-2-FURALDEHYDE

The formation of Amadori products (1-amino-1-deoxy-2-ketoses) and their subsequent decomposition to melanoidin polymers, furan derivatives, and colored substances is of considerable importance, forming the basis for the syndrome frequently referred to as the nonenzymatic browning reaction.2 In acidic solution, Amadori products are known3,4 to undergo decomposition with the production of 2-furaldehyde derivatives as the major monomeric reaction product. It has been suggested4,5 that the mechanism of this decomposition involves a 1,2 enolization of the Amadori product (I), followed by a dehydration to give the enolic form (II) of a 3-deoxy glycosulose (III), or a Schiff base thereof. In subsequent steps it has been suggested4 that II or III undergoes further dehydration to the 2-furaldehyde derivative (IV). © 1969, American Chemical Society. All rights reserved.