1.
J Enzyme Inhib
; 16(2): 107-12, 2001.
Article
in English
| MEDLINE
| ID: mdl-11342279
ABSTRACT
The synthesis and biological evaluation of a new UDP-GlcNAc competitor (I), designed to mimic the transition state of the sugar donor in the enzymatic reaction catalysed by chitin synthetase, is described. Compound (I) was found to competitively inhibit chitin synthetase from Saccharomyces cerevisiae with respect to UDP-GlcNAc, but displayed minimal antifungal activity.
Subject(s)
Aminoglycosides , Chitin Synthase/antagonists & inhibitors , Enzyme Inhibitors/pharmacology , Saccharomyces cerevisiae/enzymology , Uridine Diphosphate N-Acetylglucosamine/analogs & derivatives , Uridine Diphosphate N-Acetylglucosamine/pharmacology , Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Binding Sites , Chitin Synthase/chemistry , Enzyme Inhibitors/chemistry , Kinetics , Pyrimidine Nucleosides/pharmacology , Structure-Activity Relationship , Uridine Diphosphate N-Acetylglucosamine/chemical synthesis , Uridine Diphosphate N-Acetylglucosamine/chemistry
2.
Bioorg Med Chem Lett
; 10(13): 1483-6, 2000 Jul 03.
Article
in English
| MEDLINE
| ID: mdl-10888338
ABSTRACT
We report here the design, synthesis and antifungal evaluation of a new model of bisubstrate analogue inhibitor for glycosyltransferases. The synthetic strategy relies on the reductive amination between the aldehyde derived from an N-allylphosphono-pyrrolidine and an aminosugar.