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From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG‐chitotriomycin
Author(s) -
Despras Guillaume,
Alix Aurélien,
Urban Dominique,
Vauzeilles Boris,
Beau JeanMarie
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201406802
Subject(s) - chitin , glycoconjugate , chemistry , oxazoline , glycosylation , conjugate , glycolipid , biochemistry , combinatorial chemistry , stereochemistry , chitosan , mathematical analysis , mathematics , catalysis
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.