Document Detail

Synthesis of four diastereoisomers at carbons 24 and 25 of 3 alpha,7 alpha,12 alpha,24-tetrahydroxy-5 beta-cholestan-26-oic acid, intermediates of bile acid biosynthesis.
MedLine Citation:
PMID:  6631226     Owner:  NLM     Status:  MEDLINE    
The synthesis of four stereoisomers at C-24 and C-25 of 3 alpha,7 alpha,12 alpha,24-tetrahydroxy-5 beta-cholestan-26-oic acid is described. Pyridium chlorochromate oxidation of 3 alpha,7 alpha,12 alpha-triacetoxy-5 beta-cholan-24-ol (II) prepared from cholic acid (I) afforded 3 alpha,7 alpha,12 alpha-triacetoxy-5 beta-cholan-24-al (III) which was converted to a mixture of the four stereoisomers (IV-VII) by a Reformatsky reaction with ethyl DL-alpha-bromopropionate followed by alkaline hydrolysis. Separation of these isomers (IV-VII) was achieved by silica gel column chromatography, and subsequent reversed-phase partition column chromatography. The configurations at C-24 were elucidated by conversion of each isomer into (24R)- or (24S)-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24-tetrol (XII or XI) by Kolbe electric coupling, the C-24 configurations of which were determined by modified Horeau's method and 13C-nuclear magnetic resonance spectroscopy. The stereochemistries at C-25 were deduced by comparison of IV-VII with the products of the hydroboration followed by oxidation with alkaline hydrogen peroxide of (24E)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholest-24-en-26-oic acid (XIII).
M Une; F Nagai; K Kihira; T Kuramoto; T Hoshita
Related Documents :
10706426 - Metabolites of orally administered perilla frutescens extract in rats and humans.
2487786 - Cyclopentenoid cyanohydrin glycosides with unusual sugar residues.
7082376 - The formation of beta-glucuronidase resistant glucuronides by the intramolecular rearra...
12020346 - Oligomeric structure of proclavaminic acid amidino hydrolase: evolution of a hydrolytic...
2292586 - Generation of affinity for antithrombin iii by supplemental sulfation of heparin specie...
12392946 - Bio-smart hydrogels: co-joined molecular recognition and signal transduction in biosens...
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of lipid research     Volume:  24     ISSN:  0022-2275     ISO Abbreviation:  J. Lipid Res.     Publication Date:  1983 Jul 
Date Detail:
Created Date:  1983-12-17     Completed Date:  1983-12-17     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0376606     Medline TA:  J Lipid Res     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  924-9     Citation Subset:  IM    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Bile Acids and Salts / biosynthesis*
Chemical Phenomena
Cholestanols / chemical synthesis*,  isolation & purification
Chromatography / methods
Reg. No./Substance:
0/Bile Acids and Salts; 0/Cholestanols; 1061-64-9/3,7,12,24-tetrahydroxycholestanoic acid

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

Previous Document:  Photolabile derivatives of bile salts. Synthesis and suitability for photoaffinity labeling.
Next Document:  Differential susceptibility of mono- and di-O-alkyl ether phosphoglycerides to acetolysis.