DETECTION OF 5-HYDROXYMETHYL-2-METHYL-3(2H)-FURANONE AND OF ALPHA-DICARBONYL COMPOUNDS IN REACTION MIXTURES OF HEXOSES AND PENTOSES WITH DIFFERENT AMINES

In reaction mixtures of hexoses with primary amines, heated at pH 5 and 7, distinctly higher amounts of fragmentation products are formed in the upper pH range. To estimate the amount of fragmentation, all alpha-dicarbonyl compounds which react with omicron-phenylenediamine to quinoxaline derivatives were recorded. For the first time the alpha-dicarbonyl intermediates in a pentose amine reaction mixture were determined and the formation of 2,3,4-pentantrione was detected. The 1,4-dideoxyosone was formed from hexoses and pentoses in higher yields in the presence of alpha-amino acids, i.e. when Strecker degradation could take place. 5-Hydroxy-methyl-2-methyl-3(2H)-furanone was identified as new hexose product of Strecker degradation, and its structure established unequivocally by independent synthesis as well as by H-1 and C-13 NMR.