title: Stereoisomeric inversion of (25R)- and (25S)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acids in rat liver peroxisome.
abstract: The stereoisomeric inversion of (25R)- and (25S)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid (THCA) in rat liver peroxisome was studied. After incubation of an isomer of THCA-CoA thioester with a peroxisomal fraction, 5 beta-cholestanoic acids were extracted and optical antipodes were separated and determined by LC/APCI-MS. The transformation of (24E)-3alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholest-24-en-26-oic acid (delta 24-THCA) formed by acyl-CoA oxidase was also analyzed by GC/NICI-MS. Rapid enzymatic epimerization from either direction was observed prior to biotransformation into (24E)-delta 24-THCA.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku University, Sendai, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Ikegawa
authors.forename: T
authors.initials: T
authors.lastname: Goto
authors.forename: H
authors.initials: H
authors.lastname: Watanabe
authors.forename: J
authors.initials: J
authors.lastname: Goto
mesh_terms: D000818:Animals; D001711:Biotransformation; D002777:Cholestanols / Q000378:metabolism*; D002793:Cholic Acids / Q000378:metabolism*; D066298:In Vitro Techniques; D008099:Liver / Q000201:enzymology / Q000378:metabolism*; D013058:Mass Spectrometry; D008830:Microbodies / Q000201:enzymology / Q000378:metabolism*; D051381:Rats; D013237:Stereoisomerism
chemical_list: D002777:Cholestanols; D002793:Cholic Acids; C007426:dihydroxycoprostane; C009561:3,7,12-trihydroxycoprostane; C003681:3,7,12-trihydroxycoprostanic acid