碳-5和硫原子被乙烯基或（氟）乙烯基单元取代的S-核糖基高半胱氨酸类似物。
S-Ribosylhomocysteine analogues with the carbon-5 and sulfur atoms replaced by a vinyl or (fluoro)vinyl unit.
作者信息
Wnuk Stanislaw F, Lalama Jennifer, Garmendia Craig A, Robert Jenay, Zhu Jinge, Pei Dehua
机构信息
Department of Chemistry & Biochemistry, Florida International University, Miami, FL 33199, USA.
出版信息
Bioorg Med Chem. 2008 May 1;16(9):5090-102. doi: 10.1016/j.bmc.2008.03.028. Epub 2008 Mar 14.
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 (K(I)=96microM).
摘要
用磺酰基稳定的氟膦酸酯处理受保护的核糖或木糖5-醛得到（氟）乙烯基砜。随后进行的锡介导的脱磺酰化反应，再经过碘介导的脱锡反应，得到5,6-二脱氧-6-氟-6-碘-D-核糖或木糖己-5-烯呋喃糖。己烯呋喃糖与烷基溴化锌偶联得到含有氟代烯烃的10碳核糖基和木糖基高半胱氨酸类似物。对氟代烯基和烯基类似物进行了抑制枯草芽孢杆菌S-核糖基高半胱氨酸酶（LuxS）的评估。其中一种化合物，3,5,6-三脱氧-6-氟-D-赤藓糖己-5-烯呋喃糖，作为一种中等效力的竞争性抑制剂（K(I)=96微摩尔）。
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