Arthrobacter sp.: a lipase of choice for the kinetic resolution of racemic arylazetidinone precursors of taxanoid side chains

Tetrahedron Asymmetry

Volumn 18, Issue 9, 2007, Pages 1059-1069

  Anand, Naveen ^a   Kapoor, Munish ^a   Ahmad, Khursheed ^a   Koul, Surrinder ^a   Parshad, Rajinder ^a   Manhas, Kuldip S ^a   Sharma, Rattan L ^b   Qazi, Ghulam N ^a   Taneja, Subhash C ^a  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

^b UNIVERSITY OF JAMMU   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3 ACETOXY 1 (4 METHOXYPHENYL) 4 (2 FURANYL) 2 AZETIDINONE; 3 ACETOXY 1 (4 METHOXYPHENYL) 4 (2 THIENYL) 2 AZETIDINONE; 3 ACETOXY 1 (4 METHOXYPHENYL) 4 PHENYL 2 AZETIDINONE; 3 ACETOXY 4 (T BUTYL) 2 AZETIDINONE; AMINO ACID; ARYLAZETIDINONE; AZETIDINE DERIVATIVE; BACTERIAL ENZYME; PACLITAXEL; TAXANE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTHROBACTER; ARTICLE; BACTERIAL STRAIN; BIOLOGICAL ACTIVITY; DRUG STRUCTURE; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL; RACEMIZATION;

EID: 34249895902     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.04.031     Document Type: Article

References (49)

1. Wani M.C., Taylor H.L., Wall M.E., Coggon P., and McPhail A.T. J. Am. Chem. Soc. 93 (1971) 2325-2327
2. Saville M., Lietzau J., Pluda J., Feuerstein I., Odom J., Wilson W., Humphrey R., Feigal E., Steinberg S., and Broder S. Lancet 346 (1995) 26-28
3. In: Suffness M. (Ed). Taxol Science and Applications (1995), CRC, Boca Raton, FL
4. In: George G.I., Chen T.T., and Vyas D.M. (Eds). Taxane Anticancer Agents: Basic Science and Current Status. ACS Symposium Series 583 (1995), American Chemical Society, Washington, DC
5. Wani M.C., and Wall M.E. Cancer Res. 55 (1995) 759
6. Gou D.M., Liu Y.C., and Chen C.S. J. Org. Chem. 58 (1993) 1287-1289
7. Chen, C. S.; Gou, D. M.; Liu, Y. C. U.S. Patent 6,020,174, 2000.
8. Denis J.N., Greene A.E., Serra A.A., and Luche M.-J. J. Org. Chem. 51 (1986) 46-50
9. Denis J.N., Correa A.A., and Greene A.E. J. Org. Chem. 55 (1990) 1957-1959
10. Deng L., and Jacobson E.N. J. Org. Chem. 57 (1992) 4320-4323
11. Ojima I., Habus I., Zhao M., Georg G., and Jayasinghe L.R. J. Org. Chem. 56 (1991) 1681-1683
12. Ojima I., Habus I., Zhao M., Zucco M., Park Y.H., Sun C.M., and Brigaud T. Tetrahedron 48 (1992) 6985-7012
13. Georg G.I., Mashava P.M., Akgun K., and Milstead M.W. Tetrahedron Lett. 32 (1991) 3151-3154
14. Carr J.A., Al-Azemi T.F., Shim J.-Y., Coates C.M., Turos E., and Bisht K.S.. Tetrahedron 59 (2003) 9147-9160
15. Brieva R., Chrich J.Z., and Sih C.J. J. Org. Chem. 58 (1993) 1068-1075
16. Patel R.N. Enzyme Microb. Technol. 31 (2002) 804-826
17. Patel R.N. Curr. Opin. Biotechnol. 12 (2001) 587-604
18. Gueritte-Voegelein F., Senilh V., David B., Guenad D., and Potier P. Tetrahedron 42 (1986) 4451-4460
19. In: Morin R.B., and Gorman M. (Eds). Chemistry and Biology of β-Lactam Antibiotics Vols. 1-3 (1982), Academic Press, New York
20. SouthGate R., Brauch C., Coulton S., and Hunt E. In: Lukas G. (Ed). Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products Vol. 2 (1993), Springer, Berlin 621
21. Song C.E., Lee S.W., Roh E.J., Lee S.-g., and Le W.-K. Tetrahedron: Asymmetry 9 (1987) 983-992
22. Kim S.-C., and Kim H.-K. Bull. Korean Chem. Soc. 21 (2000) 1047-1048
23. Joshi S.N., Deshmukh A.R.A.S., and Bhawal B.M. Tetrahedron: Asymmetry 11 (2000) 1477-1485
24. Kayser M.M., Mihovilovic M.D., Kearns J., Feicht A., and Sewart J.D. J. Org. Chem. 64 (1999) 6603-6608
25. Yang Y., Drolet M., and Kayser M.M. Tetrahedron: Asymmetry 16 (2005) 2748-2753
26. Brieva R., Crich J.Z., and Sih C.J. J. Org. Chem. 58 (1993) 1068-1075
27. Patel R.N., Banerjee A., and Szarka L.J. J. Am. Oil Chem. Soc. 73 (1996) 1363-1375
28. Holtan, R. A.; Vu, P. U.S. Patent 7,067,305, 2006.
29. Patel, R. N.; Szarka, L. J.; Partyka, R. A. U.S. Patent 5,567,614, 1996.
30. Patel, R. N. U.S. Patent, 6,541,242, 2003.
31. Patel, R. N.; Szarka, L. J.; Partyka, R. A. U.S. Patent 5,811,292, 1998.
32. Patel R.N., Banerjee A., Ko R.Y., Howell J.M., Li W.S., Comzoglu F.T., Partyka R.A., and Szarka L.J. Biotechnol. Appl. Biochem. 20 (1994) 23-33
33. Basak A., Mahato T., Bhattacharya G., and Mukherjee B. Tetrahedron Lett. 38 (1997) 643-646
34. Ono C., Takao A., and Atsumi R. Biol. Pharm. Bull. 27 (2004) 345-351
35. Wyeth: Wyeth R&D Day, 2 June 2004. Presentations available at http://www.wyeth.com.
36. PanaGin Pharmaceuticals: Further information available at http://www.panagin.com.
37. Mastalerz H., Fairchild C.R., Hansel S., and Vyas D.M. Bioorg. Med. Chem. 11 (2003) 4315-4323
38. Sampath D., Discafani C.M., Loganzo F., and Beyer C. Mol. Cancer Ther. 2 (2003) 873-884. http://www.taxolog.com Taxalog: Further information available at http://www.taxolog.com
39. Shionoya M., Jimbo T., Kitagawa M., Soga T., and Tohgo A. Cancer Sci. 94 (2003) 459-466
40. Kapoor M., Anand N., Koul S., Chimni S.S., Manhas K.S., Raina C., Parshad R., Taneja S.C., and Qazi G.N. Bioorg. Chem. 31 (2003) 259-269
41. Koul S., Parshad R., Taneja S.C., and Qazi G.N. Tetrahedron: Asymmetry 14 (2003) 2459-2464 and references cited therein
42. Ahmed K., Koul S., Taneja S.C., Singh A.P., Kapoor M., Hassan R., Verma V., and Qazi G.N. Tetrahedron: Asymmetry 15 (2004) 1685-1692
43. Koul S., Koul J.L., Singh B., Kapoor M., Parshad R., Manhas K.S., Taneja S.C., and Qazi G.N. Tetrahedron: Asymmetry 16 (2005) 2575-2591
44. Koul S., Parshad R., Taneja S.C., and Qazi G.N. Tetrahedron: Asymmetry 14 (2003) 2459-2465
45. Qazi, G. N.; Parshad, R.; Koul, S.; Taneja, S. C.; Handa, S. S. U.S. Patent 6,242,243, 2001.
46. Qazi, G. N.; Parshad, R.; Koul, S.; Taneja, S. C.; Dhar, K. L.; Kotru, R. Pat. Appl. EP 952,227, 1999, Appl. 1998/302,483, 1998; Chem. Abstr. 1999, 131, 298726.
47. Koskinen A.M.P., and Klibanov A.M. Enzymatic Reactions in Organic Media (1996), Blackie, London
48. Klibanov A.M. Trends Biochem. Sci. 14 (1989) 141
49. Patel R.N., Howell J., Chidambaram R., Benoit S., and Kant J. Tetrahedron: Asymmetry 14 (2003) 3673-3677