Bioorganic Chemistry p. 283 - 296 (1997)
Update date:2022-07-30
Topics:
Milewski, SlLawomir
Hoffmann, Maria
Andruszkiewicz, Ryszard
Borowski, Edward
Several structural analogs of putative tetrahedral intermediates of the reaction catalyzed by the glutamine amide transfer domain of Candida albicans glucosamine 6-phosphate synthase have been designed and synthesized. Esters and amides of γ-phosphonic and γ-sulfonic analogs of glutamine and glutamic acid were tested as potential inhibitors of the enzyme. N-substituted amides 9 and 15 were found to be the strongest inhibitors in the series. Structure- activity relationship studies led to conclusions supporting the possibility of a direct nucleophilic attack of the glutamine amide nitrogen on an electrophilic site of the enzyme-bound fructose 6-phosphate as the most likely mechanism of nitrogen transfer in glucosamine 6-phosphate synthase.
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