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Synthesis of N ‐Acetylglucosaminyl and Diacetylchitobiosyl Amides of Heterocyclic Carboxylic Acids as Potential Chitinase Inhibitors
Author(s) -
Rottmann Antje,
Synstad Bjørnar,
Eijsink Vincent,
Peter Martin G.
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199909)1999:9<2293::aid-ejoc2293>3.0.co;2-x
Subject(s) - chemistry , amide , glycosyl , carboxylic acid , stereochemistry , acetylation , chitinase , enzyme , carboxamide , amino acid , enzyme inhibitor , oxazoline , organic chemistry , biochemistry , catalysis , gene
2‐(Dimethylamino)oxazoline‐4‐carboxylic acids 5 were prepared by condensation of binucleophilic amino acids 4 and O‐ ethyl‐ N,N ‐dimethylisourea 3 . New heterocyclic N ‐acetylglucosaminyl amides and chitobiosyl amides 8 were obtained by the coupling of tetraacetylglucosamine 6a or heptaacetylchitobiosylamine 6b with acid chlorides of heterocyclic carboxylic acids 2 or 5a and subsequent deacetylation. Based on their substitution patterns, compounds 8 were expected to have inhibitory activity towards chitinases. Enzyme assays showed that glycosyl amides 8 indeed were moderate inhibitors of chitinases, the diacetylchitobiosyl amides 8d–f generally having higher inhibitory activities than the N ‐acetylglucosaminyl amide derivatives 8a–c . Inhibitory activities depended on the chitinase tested.