From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG-chitotriomycin

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 a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-10, Vol.53 (44), p.11912-11916
Main Authors: Despras, Guillaume, Alix, Aurélien, Urban, Dominique, Vauzeilles, Boris, Beau, Jean-Marie
Format: Article
Language:English
Subjects:
Biomass
carbohydrates
Chemical Sciences
chitin
Chitin - chemistry
Glycosylation
Lipopolysaccharides - chemistry
Organic chemistry
Sugar Alcohols - chemistry
synthetic methods
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Summary: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. Short cuts from chitin: Deconstruction of chitin and selective reconstruction to give well‐defined oligosaccharides provide an effective approach to bioactive glycoconjugates. This method was applied to the preparation of the important symbiotic glycolipids.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201406802