Synthesis of N-acetylglucosaminyl and diacetylchitobiosyl amides of heterocyclic carboxylic acids as potential chitinase inhibitors
2-(Dimethylammo)oxazoline-4-carboxylic acids 5 were prepared by condensation of binucleophilic amino acids 4 and O-ethyl-N,N-dimethyhsourea 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.
Rottmann,Synstad,Eijsink,Peter
p. 2293 - 2297
(2007/10/03)
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