文章基本信息

标题：Stereospecific Dehydrogenation of (25R)-and (25S)-3α, 7α, 12α-Trihydroxy-5β-cholestanoic Acids by Acyl-CoA Oxidase in Rat Liver Light Mitochondrial Fraction
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作者：Shigeo IKEGAWA ; Hiroo WATANABE ; Takaaki GOTO 等
期刊名称：Biological and Pharmaceutical Bulletin
印刷版ISSN：0918-6158
电子版ISSN：1347-5215
出版年度：1995
卷号：18
期号：8
页码：1041-1044
DOI：10.1248/bpb.18.1041
出版社：The Pharmaceutical Society of Japan
摘要：From a stereochemical point of view, the dehydrogenation mechanism of the biotransformation of 3α, 7α, 12α-trihydroxy-5β-cholestanoic acid (THCA) into (24E)-3α, 7α, 12α-trihydroxy-5β-cholest-24-enoic acid (Δ²⁴-THCA) has been studied with capillary gas chromatography (GC)/negative ion chemical ionization (NICI)-mass spectrometry. After incubation of (24R, 25R)-or (24S, 25S)-[24, 25-²H₂] THCA, synthesized from (24E)-Δ²⁴-THCA by a deuterated diimide reduction, with a rat liver light mitochondrial fraction, 5β-cholestanoic acids were extracted and derivatized into a pentafluorobenzyl (PFB) ester-dimethylethylsilyl (DMES) ether. Subsequent resolution into THCA and Δ²⁴-THCA was attained by GC on a cross-linked 5% phenylmethyl silicone fused-silica capillary column monitored with a corresponding characteristic carboxylate anion [M-PFB]^- in the NICI mode. The stereospecific elimination of a pro-R hydrogen at C-24 in both (25R)-and (25S)-THCA indicated syn-elimination for the former, whereas anti-elimination for the latter was observed.
关键词：bile acid;dehydrogenation;cholestanoic acid;GC/MS;peroxisome;β-oxidation