HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS		QUICK SEARCH:   [advanced] Author: Keyword(s): Year:  Vol:  Page:

This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Kihira, K. Articles by Hoshita, T. Search for Related Content PubMed PubMed Citation Articles by Kihira, K. Articles by Hoshita, T. Social Bookmarking                      What's this?

Journal of Lipid Research, Vol 31, 1323-1326, Copyright © 1990 by Lipid Research, Inc.

ARTICLES

Synthesis of new bile salt analogues, sodium 3 alpha, 7 alpha-dihydroxy- 5 beta-cholane-24-sulfonate and sodium 3 alpha, 7 beta-dihydroxy-5 beta- cholane-24-sulfonate

K Kihira, M Yoshii, A Okamoto, S Ikawa, H Ishii and T Hoshita
Institute of Pharmaceutical Science, Hiroshima University School of Medicine, Japan.

This report describes the chemical synthesis of two new bile salt analogues, namely sodium 3 alpha,7 alpha-dihydroxy-5 beta-cholane-24- sulfonate and sodium 3 alpha,7 beta-dihydroxy-5 beta-cholane-24- sulfonate from chenodeoxycholic acid and ursodeoxycholic acid, respectively. Each common bile acid was converted into the corresponding 5 beta-cholane-3,7,24-triol by treatment with ethyl chloroformate in the presence of triethylamine followed by sodium borohydride reduction. Reaction of the cholanetriol with p- toluenesulfonyl chloride at 4 degrees C afforded the partially tosylated product, 24-p-toluenesulfoxy-5 beta-cholane-3,7-diol, which was then treated with sodium iodide to produce 24-iodo-5 beta-cholane- 3,7-diol. The 24-iodide was refluxed with sodium sulfite in aqueous ethanol to give the desired sulfonate analogue of the naturally occurring bile acid, chenodeoxycholic acid or ursodeoxycholic acid.
CiteULike    Complore    Connotea    Del.icio.us    Digg    Reddit    Technorati    What's this?

This article has been cited by other articles:

				T. Fujino, M. Une, T. Imanaka, K. Inoue, and T. Nishimaki-Mogami Structure-activity relationship of bile acids and bile acid analogs in regard to FXR activation J. Lipid Res., January 1, 2004; 45(1): 132 - 138. [Abstract] [Full Text] [PDF]