From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin |
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Authors: | Guillaume Despras Aurélien Alix Dominique Urban Boris Vauzeilles Jean‐Marie Beau |
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Affiliation: | 1. Université Paris‐Sud and CNRS, Laboratoire de Synthèse de Biomolécules, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR 8182, 91405 Orsay (France);2. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles du CNRS, Avenue de la Terrasse, 91198 Gif–sur–Yvette (France) |
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Abstract: | The direct and chemoselective N‐transacylation of peracetylated chitooligosaccharides (COSs), readily obtained from chitin, to give per‐N‐trifluoroacetyl derivatives offers an attractive route to size‐defined COSs and derived glycoconjugates. It involves the use of various acceptor building blocks and trifluoromethyl oxazoline dimer donors prepared with efficiency and highly reactive in 1,2‐trans glycosylation reactions. This method was applied to the preparation of the important symbiotic glycolipids which are highly active on plants and to the TMG‐chitotriomycin, a potent and specific inhibitor of insect, fungal, and bacterial N‐acetylglucosaminidases. |
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Keywords: | biomass chitin carbohydrates glycosylation synthetic methods |
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