Stereoisomeric inversion of (25R)- and (25S)-3α,7α,12α-trihydroxy-5β-cholestanoic acids in rat liver peroxisome

Shigeo Ikegawa; Takaaki Goto; Hiroo Watanabe; Junichi Goto

doi:10.1248/bpb.18.1027

Stereoisomeric inversion of (25R)- and (25S)-3α,7α,12α-trihydroxy-5β-cholestanoic acids in rat liver peroxisome

Shigeo Ikegawa, Takaaki Goto, Hiroo Watanabe, Junichi Goto

University Hospital (not affiliated with any section)

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

The stereoisomeric inversion of (25R)-and (25S)-3α, 7α, 12α-trihydroxy-5β-cholestanoic acid (THCA) in rat liver peroxisome was studied. After incubation of an isomer of THCA-CoA thioester with a peroxisomal fraction, 5β-cholestanoic acids were extracted and optical antipodes were separated and determined by LC/APCI-MS. The transformation of (24E)-3α, 7α, 12α-trihydroxy-5β-cholest-24-en-26-oic acid (Δ²⁴-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)-Δ²⁴-THCA.

Original language	English
Pages (from-to)	1027-1029
Number of pages	3
Journal	Biological and Pharmaceutical Bulletin
Volume	18
Issue number	7
DOIs	https://doi.org/10.1248/bpb.18.1027
Publication status	Published - 1995

Keywords

5β-Cholestanoic acid
APCI-MS
GC/MS
LC/MS
NICI detection
epimerization
peroxisome

ASJC Scopus subject areas

Pharmacology
Pharmaceutical Science

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title = "Stereoisomeric inversion of (25R)- and (25S)-3α,7α,12α-trihydroxy-5β-cholestanoic acids in rat liver peroxisome",

abstract = "The stereoisomeric inversion of (25R)-and (25S)-3α, 7α, 12α-trihydroxy-5β-cholestanoic acid (THCA) in rat liver peroxisome was studied. After incubation of an isomer of THCA-CoA thioester with a peroxisomal fraction, 5β-cholestanoic acids were extracted and optical antipodes were separated and determined by LC/APCI-MS. The transformation of (24E)-3α, 7α, 12α-trihydroxy-5β-cholest-24-en-26-oic acid (Δ24-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)-Δ24-THCA.",

keywords = "5β-Cholestanoic acid, APCI-MS, GC/MS, LC/MS, NICI detection, epimerization, peroxisome",

author = "Shigeo Ikegawa and Takaaki Goto and Hiroo Watanabe and Junichi Goto",

year = "1995",

doi = "10.1248/bpb.18.1027",

language = "English",

volume = "18",

pages = "1027--1029",

journal = "Biological and Pharmaceutical Bulletin",

issn = "0918-6158",

publisher = "Pharmaceutical Society of Japan",

number = "7",

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T1 - Stereoisomeric inversion of (25R)- and (25S)-3α,7α,12α-trihydroxy-5β-cholestanoic acids in rat liver peroxisome

AU - Ikegawa, Shigeo

AU - Goto, Takaaki

AU - Watanabe, Hiroo

AU - Goto, Junichi

PY - 1995

Y1 - 1995

N2 - The stereoisomeric inversion of (25R)-and (25S)-3α, 7α, 12α-trihydroxy-5β-cholestanoic acid (THCA) in rat liver peroxisome was studied. After incubation of an isomer of THCA-CoA thioester with a peroxisomal fraction, 5β-cholestanoic acids were extracted and optical antipodes were separated and determined by LC/APCI-MS. The transformation of (24E)-3α, 7α, 12α-trihydroxy-5β-cholest-24-en-26-oic acid (Δ24-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)-Δ24-THCA.

AB - The stereoisomeric inversion of (25R)-and (25S)-3α, 7α, 12α-trihydroxy-5β-cholestanoic acid (THCA) in rat liver peroxisome was studied. After incubation of an isomer of THCA-CoA thioester with a peroxisomal fraction, 5β-cholestanoic acids were extracted and optical antipodes were separated and determined by LC/APCI-MS. The transformation of (24E)-3α, 7α, 12α-trihydroxy-5β-cholest-24-en-26-oic acid (Δ24-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)-Δ24-THCA.

KW - 5β-Cholestanoic acid

KW - APCI-MS

KW - GC/MS

KW - LC/MS

KW - NICI detection

KW - epimerization

KW - peroxisome

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DO - 10.1248/bpb.18.1027

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AN - SCOPUS:0029151907

SN - 0918-6158

VL - 18

SP - 1027

EP - 1029

JO - Biological and Pharmaceutical Bulletin

JF - Biological and Pharmaceutical Bulletin

IS - 7

ER -

Stereoisomeric inversion of (25R)- and (25S)-3α,7α,12α-trihydroxy-5β-cholestanoic acids in rat liver peroxisome

Abstract

Keywords

ASJC Scopus subject areas

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