Stereochemistry of Intermediates in the Conversion of 3α,7α,12α-Trihydroxy-5ß-Cholestanoic Acid to Cholic Acid by Rat Liver Peroxisomes
- 1 February 1993
- journal article
- research article
- Published by Oxford University Press (OUP) in The Journal of Biochemistry
- Vol. 113 (2) , 141-143
- https://doi.org/10.1093/oxfordjournals.jbchem.a124017
Abstract
We have investigated the stereochemistry of the side chain of the intermediates, 3α, 7α,12α-trihydroxy-5β-cholest-24-enoic acid and 3α,7α,12α,24-tetrahydroxy-5β-cholestanoic acid, in the conversion of 3α,7α,12α-trihydroxy-5β-cholestanoic acid to cholic acid by rat liver peroxisomes. The intermediates formed were converted to the p-bromophenacyl ester derivatives and analyzed by reversed-phase high-performance liquid chromatography. Only the (24.E) form of the two isomers of the Δ24-unsaturated acid and the (24R,25S) form of the four isomers at C-24 and C-25 of the 24-hydroxy acid were found to be formed stereospecifically from either (25R)- or (25S)-3α,7α,12α-trihydroxy-5β- cholestanoic acid. Formation of the other isomers of the αβ-unsaturated bile acid or the β-hydroxy bile acid was not detected. The findings support the proposed pathway for the side-chain cleavage in cholic acid biosynthesis, which is thought to be similar to that of peroxisomal fatty acid β-oxidation.Keywords
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