文章基本信息

标题：Chemical synthesis of (22E)-3α,6β,7β-trihydroxy-5β-chol-22-en-24-oic acid and its taurine and glycine conjugates a major bile acid in the rat
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作者：Genta Kakiyama ; Takashi Iida ; Atsushi Yoshimoto 等
期刊名称：JLR Papers In Press
印刷版ISSN：0022-2275
电子版ISSN：1539-7262
出版年度：2004
卷号：45
期号：3
页码：567-573
DOI：10.1194/jlr.D300027-JLR200
语种：English
出版社：American Society for Biochemistry and Molecular Biology
摘要：A method for the synthesis of Δ²²-β-muricholic acid (Δ²²-β-MCA), (22 E )-3α,6β,7β-trihydroxy-5β-chol-22-en-24-oic acid, and its taurine and glycine conjugates (Δ²²-β-muricholyltaurine and Δ²²-β-muricholylglycine) is described. The key intermediate, 3α,6β,7β-triformyloxy-23,24-dinor-5β-cholan-22-al, was prepared from β-muricholic acid (β-MCA) via the 24-nor-22-ene and 24-nor-22,23-diol derivatives. Wittig reaction of the aldehyde with (carbomethoxymethylene) triphenylphosphorane and subsequent hydrolysis gave (unconjugated) Δ²²-β-MCA. Condensation reaction of the unconjugated acid with taurine or glycine methyl ester using diethylphosphorocyanide yielded the naturally occurring taurine or glycine conjugate ( N -acylamidate) of Δ²²-β-MCA. These synthetic reference compounds are now available for investigation of the metabolism of β-MCA by bacterial and hepatic enzymes in the rat and should also be useful as substrates for reductive deuteration or tritiation to give the 22,23-²H or ³H-β-MCA.