Document Detail


Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs.
MedLine Citation:
PMID:  8475516     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
J Shoda; M Axelson; J Sjövall
Related Documents :
11082026 - Synthesis of alpha-substituted beta-amino acids using pseudoephedrine as a chiral auxil...
10630676 - Beta-carotene generates thiobarbituric acid-reactive substances by interaction with nit...
17885836 - 27-nor-triterpenoid glycosides from the barks of zygophyllum fabago l.
11411526 - Studies on the constituents of catalpa species. vi. monoterpene glycosides from the fal...
6118466 - Glutathionuria: gamma-glutamyl transpeptidase deficiency.
18475926 - Carbonic anhydrase inhibitors. part 91. metal complexes of heterocyclic sulfonamides as...
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    
Affiliation:
Department of Physiological Chemistry, Karolinska Institutet, Stockholm, Sweden.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Bile Acids and Salts / biosynthesis*,  chemical synthesis*
Chenodeoxycholic Acid / analogs & derivatives,  chemical synthesis
Cholestenes / chemical synthesis
Cholesterol / analogs & derivatives,  chemical synthesis,  chemistry
Chromatography
Chromatography, Liquid
Deuterium*
Gas Chromatography-Mass Spectrometry
Hydroxycholesterols / chemical synthesis
Hydroxylation
Isotope Labeling*
Chemical
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

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  3 alpha-hydroxy-5 alpha-pregnan-20-one is the only active anesthetic steroid in anesthetized mouse b...
Next Document:  Sex-specific response of bone cells to gonadal steroids: modulation in perinatally androgenized fema...