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You report that the discovery of acrylamide in fried and oven-cooked food has now been explained by several research groups (C&EN, Oct. 7, page 7). It has been suggested that acrylamide arises by the Maillard reaction of glucose with asparagine [Nature, 419, 448 and 449 (2002)]. However, a team at Procter & Gamble has shown that 2-deoxyglucose, which cannot undergo the Maillard reaction, also reacts with asparagine to form acrylamide [Scientist, 16, 23 (2002)]. Although the detailed chemical process remains unknown, one plausible mechanism that is consistent with these findings involves ring opening of the initial N-glycoside (1) (see scheme below) to form imine (2). Based on the well-known chemistry of pyridoxal phosphate, imine (2) would be expected to undergo facile decarboxylation, forming a resonance-stabilized anion. Beta-elimination of the product (3) should afford acrylamide and the ammoniated saccharide |
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