Inhibition of chitin synthetase from Saccharomyces cerevisiae by a new UDP-GlcNAc analogue.
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.
Behr
J B
JB
Laboratoire de Chimie Bioorganique UMR 6519, UFR Sciences BP 1039, 51687 Reims Cedex 2, France.
Gautier-Lefebvre
I
I
Mvondo-Evina
C
C
Guillerm
G
G
Ryder
N S
NS
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000494:pharmacology; D000935:Antifungal Agents / Q000494:pharmacology; D001665:Binding Sites; D002687:Chitin Synthase / Q000037:antagonists & inhibitors* / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D007700:Kinetics; D011741:Pyrimidine Nucleosides / Q000494:pharmacology; D012441:Saccharomyces cerevisiae / Q000201:enzymology*; D013329:Structure-Activity Relationship; D014537:Uridine Diphosphate N-Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D004791:Enzyme Inhibitors; D011741:Pyrimidine Nucleosides; D014537:Uridine Diphosphate N-Acetylglucosamine; C011952:nikkomycin; C002458:polyoxorim; D002687:Chitin Synthase