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- W2051694562 abstract "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)." @default.
- W2051694562 created "2016-06-24" @default.
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- W2051694562 date "2008-05-01" @default.
- W2051694562 modified "2023-09-27" @default.
- W2051694562 title "S-Ribosylhomocysteine analogues with the carbon-5 and sulfur atoms replaced by a vinyl or (fluoro)vinyl unit" @default.
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- W2051694562 doi "https://doi.org/10.1016/j.bmc.2008.03.028" @default.
- W2051694562 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/2443868" @default.
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