Academic Journal
Chemical synthesis of (22E)-3α,6β,7β-trihydroxy-5β-chol-22-en-24-oic acid and its taurine and glycine conjugates
| العنوان: | Chemical synthesis of (22E)-3α,6β,7β-trihydroxy-5β-chol-22-en-24-oic acid and its taurine and glycine conjugates |
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| المؤلفون: | Genta Kakiyama, Takashi Iida, Atsushi Yoshimoto, Takaaki Goto, Nariyasu Mano, Junichi Goto, Toshio Nambara, Lee R. Hagey, Alan F. Hofmann |
| المصدر: | Journal of Lipid Research, Vol 45, Iss 3, Pp 567-573 (2004) |
| بيانات النشر: | Elsevier |
| سنة النشر: | 2004 |
| المجموعة: | Directory of Open Access Journals: DOAJ Articles |
| مصطلحات موضوعية: | unsaturated bile acid, tauro-Δ22-β-muricholic acid, Δ22-β-muricholyltaurine, glyco-Δ22-β-muricholic acid, Δ22-β-muricholylglycine, Biochemistry, QD415-436 |
| الوصف: | A method for the synthesis of Δ22-β-muricholic acid (Δ22-β-MCA), (22E)-3α,6β,7β-trihydroxy-5β-chol-22-en-24-oic acid, and its taurine and glycine conjugates (Δ22-β-muricholyltaurine and Δ22-β-muricholylglycine) is described. The key intermediate, 3α,6β,7β-triformyloxy-23,24-dinor-5β-cholan-22-al, was prepared from β-muricholic acid (β-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) Δ22-β-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 Δ22-β-MCA.These synthetic reference compounds are now available for investigation of the metabolism of β-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-β-MCA. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| ردمك: | 978-0-02-222752-4 0-02-222752-0 |
| تدمد: | 0022-2275 |
| Relation: | http://www.sciencedirect.com/science/article/pii/S002222752031885X; https://doaj.org/toc/0022-2275; https://doaj.org/article/b764bad6d4744d4fb87acd5b24ab17ef |
| DOI: | 10.1194/jlr.D300027-JLR200 |
| الاتاحة: | https://doi.org/10.1194/jlr.D300027-JLR200 https://doaj.org/article/b764bad6d4744d4fb87acd5b24ab17ef |
| رقم الانضمام: | edsbas.D3FFED24 |
| قاعدة البيانات: | BASE |
Full Text Finder | ردمك: | 9780022227524 0022227520 |
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| تدمد: | 00222275 |
| DOI: | 10.1194/jlr.D300027-JLR200 |