Document Detail

Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs.
MedLine Citation:
PMID:  8475516     Owner:  NLM     Status:  MEDLINE    
In connection with studies of alternative pathways in bile acid biosynthesis, potential intermediates in a pathway starting with 27-hydroxylation of cholesterol have been prepared in natural and deuterated forms. Established methods were used to prepare 27-hydroxycholesterol and 3 beta-hydroxy-5-cholestenoic acid. Clemmensen reduction of kryptogenin in unlabeled and deuterated solvents yielded 27-hydroxy-cholesterol and 16-oxo-5-cholestene-3 beta,27-diol, which were separated by adsorption chromatography on Unisil. The labeled 27-hydroxycholesterol and 3 beta-hydroxy-5-cholestenoic acid derived from it consisted of molecules with seven (50%), six (20%), and eight (20%) deuterium atoms, and unlabeled molecules were not detected. The acetates of 27-hydroxycholesterol and methyl 3 beta-hydroxy-5-cholestenoate were 7 alpha-hydroxylated in a copper-catalyzed reaction with tert-butylperbenzoate, and the products were purified by chromatography on Unisil. The 7 beta-epimers were obtained as side products. Labeled 3 beta,7 alpha-dihydroxy-5-cholenoic acid was prepared in the same way from 3 beta-hydroxy-5-[2,2,4,4,23-2H5]-cholenoic acid. The 3-oxo-delta 4 analogs of the 3 beta-hydroxy-delta 5 compounds were prepared by oxidation with cholesterol oxidase. The labeled products had the same isotopic composition as the starting materials. Gas chromatographic retention indices and mass spectral characteristics of the trimethylsilyl ether derivatives of the neutral steroids and the methylated acids are given for all compounds.
J Shoda; M Axelson; J Sjövall
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Steroids     Volume:  58     ISSN:  0039-128X     ISO Abbreviation:  Steroids     Publication Date:  1993 Mar 
Date Detail:
Created Date:  1993-05-17     Completed Date:  1993-05-17     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0404536     Medline TA:  Steroids     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  119-25     Citation Subset:  IM    
Department of Physiological Chemistry, Karolinska Institutet, Stockholm, Sweden.
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MeSH Terms
Bile Acids and Salts / biosynthesis*,  chemical synthesis*
Chenodeoxycholic Acid / analogs & derivatives,  chemical synthesis
Cholestenes / chemical synthesis
Cholesterol / analogs & derivatives,  chemical synthesis,  chemistry
Chromatography, Liquid
Gas Chromatography-Mass Spectrometry
Hydroxycholesterols / chemical synthesis
Isotope Labeling*
Reg. No./Substance:
0/Bile Acids and Salts; 0/Cholestenes; 0/Hydroxycholesterols; 115538-84-6/3,7-dihydroxy-5-cholestenoic acid; 19246-13-0/3,7-dihydroxychol-5-enoic acid; 20380-11-4/27-hydroxycholesterol; 4725-24-0/cholest-5-ene-3,7,27-triol; 474-25-9/Chenodeoxycholic Acid; 57-88-5/Cholesterol; 6561-58-6/3-hydroxy-5-cholestenoic acid; 7782-39-0/Deuterium

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