An Efficient Acylation of Free Glycosylamines for the Synthesis of<i>N</i>-Glycosyl Amino Acids and<i>N</i>-Glycosidic Surfactants for Membrane Studies

Abstract

Abstract Treatment of free glycosylamines with 3-acyl-5-methyl-1,3,4-thiadiazole-2 (3H)-thiones 6 or with acids and 5-methyl-2-thioxo-1,3,4-thiadiazole-3(2H)-carbothioic acid S-(5-methyl-1,3,4-thiadiazol-2-yl) ester 7 in hydroorganic media afforded N-acylglycosylamines in high yields and without any competitive deglycosylation. This reaction found applications in the synthesis of N-glycopeptide building blocks and of glycosidic non ionic surfactants. Results concerning surface activities of two N-acylglycosylamines are reported. The new non ionic N-octanoyl-β-D-glucosylamine surfactant exhibited efficacy and selectivity in the extraction of membrane proteins, enhanced the activity of a membrane succinate dehydrogenase and proved thus useful for membrane studies.