Conversion of 7-deoxy-10-deacetylbaccatin-III into 6-α-hydroxy-7- deoxy-10-deacetylbaccatin-III by Nocardioides luteus

Biotechnology and Applied Biochemistry

Volumn 39, Issue 2, 2004, Pages 209-214

  Hanson, Ronald L ^a   Kant, Joydeep ^a   Patel, Ramesh N ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

10 deacetylbaccatin III; Biotransformation; Hydroxylation; Paclitaxel

Indexed keywords

BIOCHEMISTRY; ENZYMES; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

ENZYME ACTIVITY; MICROBIAL STRAINS;

BIOTECHNOLOGY;

6 ALPHA HYDROXY 7 DEOXY 10 DEACETYLBACATIN III; 7 DEOXY 10 DEACETYLBACCATIN III; BACCATIN III; PACLITAXEL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME ACTIVITY; MICROBIAL ACTIVITY; MICROORGANISM; NOCARDIOIDES LUTEUS; NONHUMAN; SCREENING;

ANTINEOPLASTIC AGENTS; BIOREACTORS; BIOTRANSFORMATION; HYDROLYSIS; NOCARDIA; PILOT PROJECTS; SPECIES SPECIFICITY; TAXOIDS;

NOCARDIOIDES; NOCARDIOIDES LUTEUS;

EID: 1942536604     PISSN: 08854513     EISSN: None     Source Type: Journal    
DOI: 10.1042/BA20030093     Document Type: Article

References (43)

1. Wani, M. C., Taylon H. L., Wall, M. E., Coggon, P. and McPhail, A. T. (1971) J. Am. Chem. Soc. 93, 2325-2237
2. Levin, M. (2001 ) Drugs Today 37, 57-65
3. Lemos, P. A., Serruys, P. W. and Sousa, J. E. (2003) Circulation 107, 3003-3007
4. Schiff, P. B., Fant, J. and Horwitz, S. B. (1979) Nature (London) 277, 665-667
5. Kingston, D. G. I. (1991) Pharmacol. Ther. 52, 1-34
6. Commercon, A., Bezard, D., Bernard, F. and Bourgat, J. D. (1992) Tetrahedron Lett. 33, 5185-5188
7. Magri, N. F., Kingston, D. G. I., Jitrangsri, C. and Picarriello, T. (1986) J. Org. Chem. 51, 3239-3242
8. Denis, J., Greene, A. E., Guenard, D., Gueritte-Voegelein, F., Mangatal, L. and Potier, P. ( 1988) J. Am. Chem. Soc. 110, 5917-5919
9. Swindell, C. S., Krauss, N. E., Horwitz, S. B. and Ringel, I. (1991) J. Med. Chem. 34, 1176-1184
10. Senilh, V., Gueritte, F., Guenard, D., Colin, M. and Potier, P. (1984) C.R. Acad. Sc. Paris t. 299, Serie II, 1039-1043
11. Georg, G. I., Cheruvallath, Z. S., Himes, R. H. and Mejillano, M. R. (1992) Bioorg. Med. Chem. Lett. 2, 295-298
12. Georg, G. I., Cheruvallath, Z. S., Himes, R. H., Mejillano, M. R. and Burke, C. T. (1992) J. Med. Chem. 35, 4230-4237
13. Ojima, I., Habus, I., Zhao, M., Zucco, M., Park, Y. H., Sun, C. M. and Brigaud, T. (1992) Tetrahedron 48, 6985-7012
14. Holton, R. A. (1990) European Patent EP 400,971. Chem. Abstr. 114, 164568q
15. Holton, R. A. (1991) U.S. Patent 5,015,744. Chem. Abstr. 115, 159485b
16. Hanson, R. L., Wasylyk J. M., Nanduri, V. B., Cazzulino, D. L., Patel, R. N. and Szarka, L. J. (1994) J. Biol. Chem. 269, 22145-22149
17. Hanson, R. L., Howell, J. M., Brzozowski, D. B., Sullivan, S. A., Patel, R. N. and Szarka L. J. (1997) Biotechnol. Appl. Biochem. 26, 153-158
18. Patel, R. N., Banerjee, A., Howell, J. M., McNamee, C. G., Brzozowski, D., Mirfakhrae, D., Nanduri, V., Thottathil, J. K. and Szarka, L. J. (1994) Tetrahedron Asymmetry 4, 2069-2084
19. Kearns, J. and Kayser, M. M. (1994) Tetrahedron Lett. 35, 2845-2848
20. Patel, R. N., Banerjee, A., Ko, R. Y., Howell, J. M., Li, W., Comezoglu, F. T., Partyka, R. A. and Szarka L. J. (1994) Biotechnol. Appl. Biochem. 20, 23-33
21. Hamamoto, H., Mamedov, V. A., Kitamoto, M., Hayashi, N. and Tsuboi, S. (2000) Tetrahedron Asymmetry 11, 4485-4497
22. Wuts, P. G. M., Gu, R. L. and Northuis, J. M. (2000) Tetrahedron Asymmetry 11, 2117-2123
23. Lee, D. and Kim, M. (1998) Tetrahedron Lett. 39, 2163-2166
24. Brieva, R., Crich, J. Z. and Sih, C. J. (1993) J. Org. Chem. 58, 1068-1075
25. Gou, D. M., Liu, Y. C. and Chen, C. S. (1993) J. Org. Chem. 58, 1287-1289
26. Kumar G., Ray, S., Walle, T., Huang, Y., Willingham, M., Self, S. and Bhalla, K. (1995) Cancer Chemother Pharmacol. 36, 129-135
27. Rahman, A., Korzekwa, K. R., Grogan, J., Gonzalez, F. J. and Harris, J. W. (1994) Cancer Res. 54, 5543-5546
28. Harris, J. W., Katki, A., Anderson, L. W., Chmurny G. N., Paukstelis, J. V. and Collins, J. M. (1994) J. Med. Chem. 37, 706-709
29. Sparreboom, A., Huizing, M. T., Boesen, J. J. B., Nooijen, W. J., van Tellingen, O. and Beijnen J. H. (1995) Cancer Chemother. Pharmacol. 36, 299-304
30. Monsarrat B., Royer, I., Wright M. and Cresteil, T. (1997) Bull. Cancer 84, 125-133
31. Smith, R. V. and Rosazza, J. P. (1974) Arch. Biochem. Biophys. 161, 551-558
32. Walker, K. and Croteau, R. B. (2001) Phytochemistry 58, 1-7
33. Schoendorf, A., Rithner C. D., Williams, R. M. and Croteau, R B. (2001) Proc. Natl. Acad. Sci. U.S.A. 98, 1501-1506
34. Jennewein, S., Rithner, C. D., Williams, R. M. and Croteau, R. B. (2001) Proc. Natl. Acad. Sci. U.S.A. 98, 13595-13600
35. Hefner, J., Rubenstein, S. M., Ketchum, R. E. B., Gibson, D. M., Williams, R. M. and Croteau, R. B. (1996) Chem. Biol. 3, 479-489
36. Hu, S., Tian, X., Zhu, W. and Fang, Q. (1996) Tetrahedron 52, 8739-8746
37. Hu, S., Tian, X., Zhu, W. and Fang, Q. (1996) J. Nat. Prod. 59, 1006-1009
38. Hu, S., Sun, D., Tian, X. and Fang, Q. (1997) Tetrahedron Lett. 38, 2721-2724
39. Hu, S., Tian, X., Zhu, W. and Fang, Q. (1997) Biocatal. Biotransform. 14, 241-250
40. Hu, S., Tian, X., He, W. Y., Kong, M., Sun, D. A. and Fang, Q. (1998) Chinese Chem. Lett. 9, 39-43
41. Hu, S., Sun, D. and Scott, A. I. (2000) Tetrahedron Lett. 41, 1703-1705
42. Hu, S., Sun, D., Tian, X. and Fang, Q. (2002) Chirality 14, 495-497
43. Chen, T.S., Li, X., Bollag, D., Liy, Y. and Chang, C. (2001) Tetrahedron Lett. 42, 3787-3789