S-Ribosylhomocysteine analogues with the carbon-5 and sulfur atoms replaced by a vinyl or (fluoro)vinyl unit
Treatment of the protected ribose or xylose 5-aldehyde with sulfonyl-stabilized fluorophosphonate gave (fluoro)vinyl sulfones. Stannyldesulfonylation followed by iododestannylation afforded 5,6-dideoxy-6-fluoro-6-iodo-d-ribo or xylo-hex-5-enofuranoses. Coupling of the hexenofuranoses with alkylzinc bromides gave 10-carbon ribosyl- and xylosylhomocysteine analogues incorporating a fluoroalkene. The fluoroalkenyl and alkenyl analogues were evaluated for inhibition of Bacillus subtilis S-ribosylhomocysteinase (LuxS). One of the compounds, 3,5,6-trideoxy-6-fluoro-d-erythro-hex-5-enofuranose, acted as a competitive inhibitor of moderate potency (KI = 96 μM).
Novel S-ribosylhomocysteine analogues as potential inhibitors of LuxS enzyme
(Chemical Equation presented) Selective cross-coupling of the protected 6-fluoro-6-iodo-α-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-α/β-D-ribo- dec-5(Z)-enofuranuronate; a S-ribosylhomocysteine analogue with the sulfur and carbon-5 atoms replaced by the fluoro(vinyl) unit. Copyright Taylor & Francis Group, LLC.
Wnuk, Stanislaw F.,Lalama, Jennifer,Robert, Jenay,Garmendia, Craig A.
p. 1051 - 1055
(2008/09/16)
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