Synthesis of new (difluoromethylphosphono)azadisaccharides designed as bisubstrate analogue inhibitors for GlcNAc:beta-1,4 glycosyltransferases.
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.
Gautier-Lefebvre
I
I
Laboratoire de Chimie Bioorganique UMR 6519, UFR Sciences BP 1039, Reims, France.
Behr
J B
JB
Guillerm
G
G
Ryder
N S
NS
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002687:Chitin Synthase / Q000037:antagonists & inhibitors; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016695:Glycosyltransferases / Q000037:antagonists & inhibitors*; D003904:Mitosporic Fungi / Q000187:drug effects; D015394:Molecular Structure; D012441:Saccharomyces cerevisiae / Q000187:drug effects / Q000201:enzymology
D000935:Antifungal Agents; D001372:Aza Compounds; D004187:Disaccharides; D004791:Enzyme Inhibitors; D016695:Glycosyltransferases; D002687:Chitin Synthase