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Originally published In Press as doi:10.1194/jlr.D300027-JLR200 on December 1, 2003

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Journal of Lipid Research, Vol. 45, 567-573, March 2004
Copyright © 2004 by American Society for Biochemistry and Molecular Biology

Methods

Chemical synthesis of (22E)-3{alpha},6ß,7ß-trihydroxy-5ß-chol-22-en-24-oic acid and its taurine and glycine conjugates

: a major bile acid in the rat

Genta Kakiyama*, Takashi Iida1,*, Atsushi Yoshimoto*, Takaaki Goto{dagger}, Nariyasu Mano{dagger}, Junichi Goto{dagger}, Toshio Nambara{dagger}, Lee R. Hagey§ and Alan F. Hofmann§

* Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo 156-8550, Japan
{dagger} Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan
§ Department of Medicine, University of California, San Diego, La Jolla, California 92093-0813

1 To whom correspondence should be addressed. e-mail: takaiida{at}chs.nihon-u.ac.jp

A method for the synthesis of {Delta}22-ß-muricholic acid ({Delta}22-ß-MCA), (22E)-3{alpha},6ß,7ß-trihydroxy-5ß-chol-22-en-24-oic acid, and its taurine and glycine conjugates ({Delta}22-ß-muricholyltaurine and {Delta}22-ß-muricholylglycine) is described. The key intermediate, 3{alpha},6ß,7ß-triformyloxy-23,24-dinor-5ß-cholan-22-al, was prepared from ß-muricholic acid (ß-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-ß-MCA. Condensation reaction of the unconjugated acid with taurine or glycine methyl ester using diethylphosphorocyanide yielded the naturally occurring taurine or glycine conjugate (N-acylamidate) of {Delta}22-ß-MCA.

These synthetic reference compounds are now available for investigation of the metabolism of ß-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-ß-MCA.

Abbreviations: DEPC, diethylphosphorocyanide; EI, electron ionization; ESI, electrospray ionization; EtOAc, ethyl acetate; HR-MS, high-resolution mass spectra; IR, infrared; LR-MS, low-resolution mass spectra; ß-MCA, ß-muricholic acid; {Delta}22-ß-MCA, {Delta}22-ß-muricholic acid; NIM, negative ion mode; PIM, positive ion mode; UDCA, ursodeoxycholic acid; {Delta}22-UDCA, {Delta}22-ursodeoxycholic acid

Supplementary key words unsaturated bile acid • tauro-{Delta}22-ß-muricholic acid • {Delta}22-ß-muricholyltaurine • glyco-{Delta}22-ß-muricholic acid • {Delta}22-ß-muricholylglycine


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