N-3-oxoacyl derivatives of L-2,3-diaminopropanoic acid and their peptides;Novel inhibitors of glucosamine-6-phosphate synthase

Citation
R. Andruszkiewicz et al., N-3-oxoacyl derivatives of L-2,3-diaminopropanoic acid and their peptides;Novel inhibitors of glucosamine-6-phosphate synthase, J ENZ INHIB, 15(5), 2000, pp. 429
Citations number
22
Categorie Soggetti
Biochemistry & Biophysics
Journal title
JOURNAL OF ENZYME INHIBITION
ISSN journal
87555093 → ACNP
Volume
15
Issue
5
Year of publication
2000
Database
ISI
SICI code
8755-5093(2000)15:5<429:NDOLAA>2.0.ZU;2-7
Abstract
Novel inhibitors 1-4 of glucosamine-6-phosphate synthase from Candida albic ans have been designed based on acylation of the N3 amino group of L-2,3-di aminopropanoic acid with the corresponding ketoacids. These inhibitors have been shown to alkylate the fungal enzyme in a time-dependent manner. Compo und 3 containing trans-beta-benzoyl acrylic acid as an acyl residue was fou nd to be the most potent inhibitor in the series. Dipeptides composed of th e active inhibitors and norvaline demonstrated potent antifungal activity a gainst selected strains of Candida spp. and Saccharomyces cerevisiae. Their activity was reversed upon addition of N-acetylglucosamine to the medium.