J. Lipid Res. Neurobiology of Lipids (ISSN1683-5506)
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A more recent version of this article appeared on March 1, 2004

Papers In Press, published online ahead of print December 1, 2003
J. Lipid Res., doi:10.1194/jlr.D300027-JLR200
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Submitted on September 22, 2003
Revised on November 18, 2003
Accepted on November 18, 2003

Chemical synthesis of (22E)-3alpha ,6beta ,7beta -trihydroxy-5beta -chol- 22-en-24-oic acid and its taurine and glycine conjugates: A major bile acid in the rat

Genta Kakiyama, Takashi Iida, Atsushi Yoshimoto, Takaaki Goto, Nariyasu Mano, Junichi Goto, Toshio Nambara, Lee R. Hagey, and Alan F. Hofmann

Department of Chemistry, Nihon University, College of Humanities and Science, Setagaya, Tokyo 156-8550

Corresponding Author: takaiida{at}chs.nihon-u.ac.jp

A method for the synthesis of delta 22-beta -muricholic acid (delta 22-beta -MCA), (22E)-3alpha ,6beta ,7beta -trihydroxy-5beta -chol-22-en-24-oic acid, and its taurine and glycine conjugates is described. The key intermediate, 3alpha ,6beta ,7beta -triformyloxy-23,24-dinor-5beta -cholan-22-al, was prepared from beta -muricholic acid (beta -MCA) via the 24-nor-22-ene and 24-nor-22,23-diol derivatives. Wittig reaction of the aldehyde with (carbomethoxymethylene)triphenylphosphorane and subsequent hydrolysis gave (unconjugated) delta 22-beta -MCA. Condensation reaction of the unconjugate with taurine or glycine methyl ester using diethylphosphorocyanide yielded the naturally occurring taurine or glycine conjugate (N-acylamidate) of {delta22}-beta -MCA. These synthetic reference compounds are now available for investigation of the metabolism of beta -MCA by bacterial and hepatic enzymes in the rat and should also be useful as substrates for reductive deuteration or tritiation to give the 22,23-2H or 3H-beta -MCA.


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