Synthesis of 3 α,7 α,14 α-trihydroxy-5 β-cholan-24-oic acid: A potential primary bile acid in vertebrates

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 3, 2004, Pages 371-374

  Kakiyama, Genta ^a   Iida, Takashi ^a   Goto, Takaaki ^b   Mano, Nariyasu ^b   Goto, Junichi ^b   Nambara, Toshio ^b  

^a NIHON UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

3 ,7 ,14 trihydroxy 5 cholan 24 oic acid; Dimethyldioxirane; Remote hydroxylation

Indexed keywords

3ALPHA,7ALPHA,14ALPHA TRIHYDROXY 5BETA CHOLAN 24 OIC ACID; ALCOHOL DERIVATIVE; ALUMINUM OXIDE; BILE ACID; CHENODEOXYCHOLIC ACID DERIVATIVE; CHROMIC ACID; DIMETHYLDIOXIRANE; ESTER DERIVATIVE; KETONE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG; URSODEOXYCHOLIC ACID; ZINC DERIVATIVE; 3,7,14 TRIHYDROXYCHOLANOIC ACID; 3,7,14-TRIHYDROXYCHOLANOIC ACID; CHOLIC ACID DERIVATIVE;

ACIDITY; ADSORPTION; ARTICLE; BILE; BILE ACID METABOLISM; BILE ACID SYNTHESIS; HYDROXYLATION; PH; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; VERTEBRATE; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ANIMALS; BILE ACIDS AND SALTS; CHOLIC ACIDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM; VERTEBRATES;

EID: 4544311113     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.52.371     Document Type: Article

References (22)

1. Part 25 of this series: Iida T., Hikosaka M., Kakiyama G., Shiraishi K., Schteingart C. D., Hagey L. R., Ton-Nu H. T., Hofmann A. F., Mano N., Goto J., Nambara T., Chem. Pharm. Bull., 50, 1327-1334 (2002).
2. Hofmann A. F., Schteingart C. D., Hagey L. R., "Bile Acids in Liver Diseases," ed. by Paumgartner G., Beuers U., Kluwer Academic Publishers, Dordrecht, 1995, pp. 3-30.
3. Haslewood G. A. D., Sjövall J., Biochem. J., 57, 126-130 (1954).
4. Hsia S. L., "The Bile Acids-Chemistry, Physiology, and Metabolism," Vol. 1, ed. by Nair P. P., Kritchevsky D., Plenum Press, New York, 1971, pp. 95-120.
5. Lee S. P., Lester R., Pyrek J. St., J. Lipid Res., 28, 19-31 (1987).
6. Hagey L. R., Schteingart C. D., Ton-Nu H.-T., Hofmann A. F., J. Lipid Res., 35, 2041-2048 (1994).
7. Shoda J., Mahara R., Osuga T., Tohma M., Ohnishi S., Miyazaki H., Tanaka N., Matsuzaki Y., J. Lipid Res., 29, 847-858 (1988).
8. Dumaswala R., Setchell K. D. R., Zimmer-Nechemias L., Iida T., Goto J., Nambara T., J. Lipid Res., 30, 847-856 (1989).
9. Schteingart C. D., Hagey L. R., Setchell K. D. R., Hofmann A. F., J. Biol. Chem., 268, 11239-11246 (1993).
10. Hagey L., Schteingart C. D., Ton-Nu H.-T., Hofmann A. F., J. Lipid Res., 43, 685-690 (2002).
11. Hoshita T., Hirofugi S., Kazuno T., J. Biochem. (Tokyo), 51, 136-141 (1967).
12. Haslewood G. A. D., Biochem. J., 78, 352-359 (1961).
13. Klinot J., Jirsa M., Klinotova E., Ubik K., Protiva J., Collect. Czecho. Chem. Commun., 51, 1722-1730 (1986).
14. Hagey L. R., Schteingart C. G., Ton-Nu H.-T., Odell D., Hofmann A. F., The Condor, 92, 593-597 (1990).
15. Hagey L. R., Thesis Ph. D., "Bile Acid Biodiversity in Vertebrates: Chemistry and Evolutionary Implications," University of California, San Diego, 1992.
16. Cerré C., Hofmann A. F., Schteingart C. D., Jia W., Maltby D., Tetrahedron, 53, 435-446 (1997).
17. Iida T., Yamaguchi T., Nakamori R., Hikosaka M., Mano N., Goto J., Nambara T., J. Chem. Soc. Perkin Trans. 1, 2001, 2229-2236 (2001).
18. Hashimoto N., Aoyama T., Shioiri T., Chem. Pharm. Bull., 29, 1475-1478 (1981).
19. Iida T., Nambara T., Chang F. C., "Bile Acids in Gastroenterology," ed. by Hofmann A. F., Paumgartner G., Stiehl A., Kluwer Academic Publishers, Dordrecht, 1995, pp. 8-26.
20. Sasaki T., Nakamori R., Yamaguchi T., Kasuga Y., Iida T., Nambara T., Chem. Phys. Lipids, 109, 135-143 (2001).
21. Cheng Y.-S., Liu W.-L., Chen S.-H., Synthesis, 1980, 223-224 (1980).
22. Gensler W. J., Johnson F., Sloan A. D. B., J. Am. Chem. Soc., 82, 6074-6081 (1960).