An Efficient Acylation of Free Glycosylamines for the Synthesis of N-Glycosyl Amino Acids and N-Glycosidic Surfactants for Membrane Studies |
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| Authors: | Daniel Plusquellec Catherine Brenner-Hénaff Pascale Léon-Ruaud Stéphane Duquenoy Martine Lefeuvre Henri Wróblewski |
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| Institution: | 1. ENSCR, Département de Chimie Organique , Laboratoire de Synthèses et Activations de Biomolécules, associé , au CNRS URA D1467, Avenue du Général Leclerc, 35700 , Rennes , France;2. Université de Rennes I, Département “Membranes et Osmorégulations”, Laboratoire d'Immunochimie des Membranes Bactériennes, associé , au CNRS URA D0256, Campus de Beaulieu, 35042 , Rennes cedex , France |
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| 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. |
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