title: From chitin to bioactive chitooligosaccharides and conjugates: access to lipochitooligosaccharides and the TMG-chitotriomycin.
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.
authors.affiliation: Université Paris-Sud and CNRS, Laboratoire de Synthèse de Biomolécules, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR 8182, 91405 Orsay (France).
authors.forename: Guillaume
authors.initials: G
authors.lastname: Despras
authors.forename: Aurélien
authors.initials: A
authors.lastname: Alix
authors.forename: Dominique
authors.initials: D
authors.lastname: Urban
authors.forename: Boris
authors.initials: B
authors.lastname: Vauzeilles
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Beau
mesh_terms: D018533:Biomass; D002686:Chitin / Q000737:chemistry*; D006031:Glycosylation; D008070:Lipopolysaccharides / Q000737:chemistry*; D013402:Sugar Alcohols / Q000737:chemistry*
chemical_list: D008070:Lipopolysaccharides; D013402:Sugar Alcohols; C528826:TMG-chitotriomycin; C023023:lipid-linked oligosaccharides; D002686:Chitin
keywords: biomass; carbohydrates; chitin; glycosylation; synthetic methods