Novel S-ribosylhomocysteine analogues as potential inhibitors of LuxS enzyme.
Selective cross-coupling of the protected 6-fluoro-6-iodo-alpha-D-ribo-hex-5-enofuranose with 2 equivalents of 4-ethoxy-4-oxobutylzinc bromide in the presence of Pd[P(Ph)(3)](4) followed by deprotections gave methyl 5,6,7,8,9-pentadeoxy-6-fluoro-alpha/beta-D-ribo-dec-5(Z)-enofuranuronate; a S-ribosylhomocysteine analogue with the sulfur and carbon-5 atoms replaced by the fluoro(vinyl) unit.
Department of Chemistry & Biochemistry, Florida International University, Miami, Florida 33199, USA. wnuk@fiu.edu
Stanislaw F
SF
Wnuk
Jennifer
J
Lalama
Jenay
J
Robert
Craig A
CA
Garmendia
D001426:Bacterial Proteins / Q000037:antagonists & inhibitors*; D013437:Carbon-Sulfur Lyases / Q000037:antagonists & inhibitors*; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006710:Homocysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; C487472:S-ribosyl-L-homocysteine; D006710:Homocysteine; D013437:Carbon-Sulfur Lyases; C117753:LuxS protein, Bacteria