First chemical synthesis, aggregation behavior and cholesterol solubilization properties of pythocholic acid and 16α-hydroxycholic acid

European Journal of Organic Chemistry

Volumn , Issue 20, 2007, Pages 3331-3336

  Nonappa, ^a   Maitra, Uday ^a,b  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

Critical micellar concentration; Oxidation; Pythocholic acid; Regio and chemoselective; Remote functionalization

Indexed keywords

EID: 34447543983     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700211     Document Type: Article

References (36)

1. a) H. Danielsson, in The Bile Acids: Chemistry, Physiology and Melabolsm (Eds.: P. P. Nair, D. Kritchevsky), Plenum Press, New York, 1973, vol. 2, pp. 1-32;
2. b) S. Mukhopadhyay, U. Maitra, Curr. Sci. 2004, 87, 1666-1683;
3. c) A. Enhsen, W. Kramer, G. Wess, Drug Discovery Today 1998, 3, 409-418.
4. a) A. F. Hofmann, Biochem. J. 1963, 89, 57-68;
5. b) M. C. Carey, Ann. Rev. Physiol. 1983, 45, 651-677.
6. a) G. A. D. Haselwood, Biol. Rev. 1964, 39, 537-574;
7. b) T. Iida, M. Hikosaka, G. Kakiyama, K. Shiraishi, C. D. Schteingart, L. R. Hagey, H. T. Ton-Nu, A. F. Hofmann, N. Mano, J. Goto, T. Nambara, Chem. Pharm. Bull. 2002, 50, 1327-1334.
8. a) A. Moschetta, A. L. Bookout, D. J. Mangelsdorf, Nat. Med. 2004, 10, 1352-1358;
9. b) M. Watanabe, M. S. Houten, C. Mataki, M. A. Christoffolete, B. W. Kim, H. Sato, N. Messaddeq, J. W. Harney, O. Ezaki, T. Kodama, K. Schoonjans, A. C. Bianco, J. Auwerx, Nature 2006, 439, 484-489;
10. c) D. L. Motola, C. L. Cummins, V. Rottiers, K. K. Sharma, T. Li, Y. Li, K. S. Powell, H. E. Xu, R. J. Auchus, A. Antebi, D. J. Mangelsdorf, Cell 2006, 124, 1209-1223.
11. a) G. A. D. Haslewood, V. Wootton, Biochem. J. 1951, 49, 67-71;
12. b) G. A. D. Haslewood, V. Wootton, Biochem. J. 1950, 47, 584-597;
13. c) M. Kuroda, H. Arata, J. Biol. Chem. 1951, 29, 225-226.
14. S. Bergström, H. Danielsson, T. Kazuno, J. Biol. Chem. 1960, 235, 983-988.
15. M. Kimura, M. Kawata, A. Fujino, K. Yamasaki, Tetrahedron Lett. 1970, 23, 2021-2024.
16. L. R. Hagey, C. D. Schteingart, H. T. Ton-Nu, A. F. Hofmann, J. Lipid Res. 2002, 43, 685-690.
17. S. Mukhophadhyay, U. Maitra, Org. Lett. 2004, 6, 31-34.
18. a) R. Breslow, P. White, J. Am. Chem. Soc. 1990, 112, 6842-6847;
19. b) R. Breslow, Acc. Chem. Res. 1980, 13, 170-177.
20. V. Schwarz, P. Pihera, J. Halasková, Cesk. Farm. 1984, 33, 327-330.
21. R. V. Oppenauer, Monatsh. Chem. 1966, 97, 62-66.
22. K. Kato, M. Sugahara, N. Tohnai, K. Sada, M. Miyata, Cryst. Growth Des. 2004, 4, 263-272.
23. a) I. Saraogi, V. G. Vijay, S. Das, K. Sekar, T. N. Guru Row, Cryst. Eng. 2003, 6, 69-77;
24. b) M. D. Prasanna, T. N. Guru Row, Cryst. Eng. 2000, 3, 135-154;
25. c) P. Metrangolo, T. Pilati, G. Resnati, CrystEngComm 2006, 8, 946-947.
26. J. Einhorn, C. Einhorn, F. Ratajczak, J. L. Piere, J. Org. Chem. 1996, 61, 7452-7454.
27. M. F. Semmelhack, C. R. Schmidt, D. A. Cortes, C. S. Chou, J. Am. Chem. Soc. 1984, 106, 3374-3376.
28. B. Matkovics, B. Samuelsson, Acta Chem. Scand. 1962, 16, 683-688.
29. H. Minion, J. Am. Chem. Soc. 1946, 68, 2487-2488.
30. C. D. Schteingart, A. F. Hofmann, personal communication.
31. K. Kalyanasundaran, J. K. Thomas, J. Am. Chem. Soc. 1977, 99, 2039-2044.
32. a) M. C. Carey, J. C. Montent, M. C. Phillips, M. J. Armstrong, N. A. Mazer, Biochemistry 1981, 20, 3637;
33. b) K. Matsuoka, Y. Kuranaga, Y. Moroi, Biochim. Biophys. Acta 2002, 1580, 200-214.
34. th ed., Addison Wesley Longman Limited, Harlow, England, 1996, pp. 931.
35. L. F. Fieser, S. Rajagopalan, J. Am. Chem. Soc. 1949, 71, 3935-3938.
36. R. Hirschmann, N. L. Wendler, J. Am. Chem. Soc. 1953, 75, 2361-2364.