SYNTHESIS OF N-(1-DEOXYHEXITOL-1-YL)AMINO ACIDS, REFERENCE COMPOUNDS FOR THE NONENZYMIC GLYCOSYLATION OF PROTEINS

Article abstract of DOI:10.1016/0008-6215(84)85082-X

The N-(1-deoxy-D-mannitol-1-yl) and N-(1-deoxy-D-glucitol-1-yl) derivatives of L-valine, L-alanine, L-threonine, and L-leucine were prepared by reductive amination of D-mannose and D-glucose with appropriate amino acids, in the presence of sodium cyanoborohydride.N^ε-(1-deoxy-D-mannitol-1-yl)- and N^ε-(1-deoxy-D-glucitol-1-yl)-L-lysine were prepared by similar reactions of hexoses with N^α-tert-butoxycarbonyl and N^α-benzyloxycarbonyl-L-lysine, followed by removal of the protecting groups.The structures were confirmed by (1)H-n.m.r. spectroscopy, which showed that each compound was completely free of its C-2 epimer.The synthetic compounds may be used as reference compounds for the identification of N-(1-deoxyhexitol-1-yl)amino acids formed when N-(1-deoxy-D-fructose-1-yl) groups of nonenzymically glycosylated proteins, of the hemoglobin A_1c type, are reduced with sodium borohydride, and the protein is subjected to acid-catalyzed hydrolysis.