Thioimidoyl furanosides as first inhibitors of the alpha-L-arabinofuranosidase AbfD3.
Two sets of five thioimidoyl alpha-L-arabino- and beta-D-galactofuranosides were designed, synthesized and subjected to docking studies to evaluate their ability to be recognized by the active site of the alpha-L-arabinofuranosidase AbfD3. Further in vitro assays showed that the targeted furanosides are the first potent inhibitors of this furanosyl hydrolase and that the most efficient one, the thiazolyl alpha-L-arabinofuranoside 1, is a competitive inhibitor having a KI of 1.4 microM.
Lopez
Gérald
G
Ecole Nationale Supérieure de Chimie de Rennes, UMR CNRS 6226, Team Organic Synthesis and Organized Systems, Avenue du Général Leclerc, F-35700 Rennes, France.
Daniellou
Richard
R
O'Donohue
Michael
M
Ferrières
Vincent
V
Nugier-Chauvin
Caroline
C
D001419:Bacteria / Q000201:enzymology; D002855:Chromatography, Thin Layer; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D007700:Kinetics; D008958:Models, Molecular; D013329:Structure-Activity Relationship
D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D006026:Glycoside Hydrolases; C019713:alpha-N-arabinofuranosidase