The Amadori Rearrangement Product as an Intermediate in the Browning Reaction

Part I. Preparation and Infrared Spectra of 1-Amino-l-deoxy-D-fructoses and 1-Glycino-l-deoxy-D-tagatose

抄録

In relation to the elucidation of the mechanism of the browning reaction, isolation in crystalline form, structure and characterization of the intermediate compounds are studied. Glycine-isoglucos-amine (1-deoxy-l-glycino-D-fructose) was prepared in crystalline form by conversions of glycine-N-D-glucoside and -N-D-mannoside (both Na salt) and also from heated solLion of glycine and D-glucose. Similarly, crystalline glycine-isogalactosamine (I-deoxy-l-glycino-D-tagatose) (m.p. 165_??_168°C) was obtained by rearrangement of glycine-N-D-galactoside (Na salt) and from the browning mixture of glycine and D-galactose. Infrared studies indicated that the absorption near 3, 500 cm -1 is characteristic to isoglucosamines but not to isogalactsamine. On the infrared and periodate oxidation data, the structure of the amino acid-isoglycosamines is considered.