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Synthesis of N-Acetylglucosaminyl and Diacetylchitobiosyl Amides of Heterocyclic Carboxylic Acids as Potential Chitinase Inhibitors

✍ Scribed by Antje Rottmann; Bjørnar Synstad; Vincent Eijsink; Martin G. Peter

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
193 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

2-(Dimethylamino)oxazoline-4-carboxylic acids 5 were compounds 8 were expected to have inhibitory activity towards chitinases. Enzyme assays showed that glycosyl prepared by condensation of binucleophilic amino acids 4 and O-ethyl-N,N-dimethylisourea 3. New heterocyclic N-amides 8 indeed were moderate inhibitors of chitinases, the diacetylchitobiosyl amides 8d-f generally having higher acetylglucosaminyl amides and chitobiosyl amides 8 were obtained by the coupling of tetraacetylglucosamine 6a or inhibitory activities than the N-acetylglucosaminyl amide derivatives 8a-c. Inhibitory activities depended on the heptaacetylchitobiosylamine 6b with acid chlorides of heterocyclic carboxylic acids 2 or 5a and subsequent chitinase tested. deacetylation. Based on their substitution patterns, tained recently by molecular modelling of the binding inter-

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