Efficient regioselective chemical modifications of maltotriose: an easy access to oligosaccharidic scaffold |
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Authors: | Thiebault Nicolas Lesur David Godé Paul Moreau Vincent Djedaïni-Pilard Florence |
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Institution: | Laboratoire des Glucides, CNRS-UMR 6219, Institut de Chimie de Picardie, Université de Picardie Jules Verne, 33 rue St Leu, 80039 Amiens, France |
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Abstract: | Regioselective chlorination of fully unprotected maltotriose has given in high yield 1I,2I-III,3I-III,4III-octa-O-acetyl-6I-III-trichloro-6I-III-trideoxymaltotriose. Moreover, regioselective ditritylation of methyl β-maltotrioside has provided the two regioselectively C6-disubstituted trisaccharides. Selective deprotection of these new compounds gives the corresponding diol and halogenated analogues, respectively, in good yield. All compounds have been completely characterized and the substitution pattern in the oligosaccharidic sequence has been elucidated. A new family of amphiphilic carbohydrates, namely the 6-deoxy-6-alkylthiomaltotriose derivatives, bearing either two or three thioalkyl hydrophobic chains, respectively, has been synthesized. Critical micellar concentration (CMC) values as well as the antimicrobial properties have been evaluated for amphiphilic compounds. |
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Keywords: | Di-halogeno-di-6-deoxymaltotriose Di-alkyl-di-6-deoxymaltotriose NMR characterization Antimicrobial activity |
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