Enzymatic acetylation of 10-deacetylbaccatin III to baccatin III by C-10 deacetylase from Nocardioides luteus SC 13913

Enzyme and Microbial Technology

Volumn 27, Issue 6, 2000, Pages 371-375

  Patel, Ramesh N ^a   Banerjee, Amit ^a   Nanduri, Venkata ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; AROMATIC POLYMERS; BIOCONVERSION; BIOSYNTHESIS; CATALYST ACTIVITY; CELLULOSE DERIVATIVES; ENZYME IMMOBILIZATION; PH EFFECTS; POLYOLEFINS;

ACYL DONOR; DEACETYLBACCATIN;

ENZYME KINETICS;

ACYLTRANSFERASE; PACLITAXEL;

ACETYLATION; ACTINOBACTERIA; ARTICLE; BIOTRANSFORMATION; CATALYSIS; DRUG SYNTHESIS; ENVIRONMENTAL TEMPERATURE; ENZYME ANALYSIS; ENZYME IMMOBILIZATION; NOCARDIODES LUTEUS; NONHUMAN; PH; REACTION ANALYSIS;

ACTINOBACTERIA (CLASS); NOCARDIOIDES LUTEUS; UNCULTURED ACTINOMYCETE;

EID: 0034284736     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(00)00235-0     Document Type: Article

References (27)

1. Wall M.E., Wani M.C., Taylor H.L. Isolation and chemical characterization of antitumor agents from plants. Cancer Treat Rep. 60:1976;1011-1014.
2. Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 1971;93:2325-7.
3. Schiff P.B., Fant J., Horwitz S.B. Promotion of microtubule assembly in vitro by taxol. Nature. 227:1979;9479-9490.
4. Kingston G.D.I. Natural taxoids structure and chemistry . Suffness M. Taxol science and applications . 1995;287-315 CRC, Boca Raton, FL.
5. Suffness M. Taxol from discovery to therapeutic use . Ann Rep Med Chem. 28:1993;305-315.
6. Vidensek N., Lim P., Campbell A., Carlson C. Taxol content in bark, wood, root, leaf, twig, and seedling from several Taxus species. J Nat Prod. 53:1990;1609-1615.
7. Croom E.M. Taxus for taxol and taxoids. Suffness M. Taxol science and applications . 1995;37-70 CRC, Boca Raton, FL.
8. Christen AA, Gibson DM, Bland J. US Patent 5019504, 1991.
9. Gibson D.M., Ketchum E.B., Hirasuna T.J., Shuler M.L. Potential of plant cell culture for taxane production. Suffness M. Taxol science and applications . 1995;71-95 CRC, Boca Raton, FL.
10. Stierle, A, Strobel GA, Stierle D. Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew. Science 1993;260:214-6.
11. Denis J.-N., Greene A.E., Guenard D., Gueritte-Vogelin F., Mangatal L., et al. Highly efficient, practical approach to natural taxol. J Am Chem Soc. 110:1988;5917-5921.
12. Holton RA, Biediger RJ. US Patent 5243045, 1993.
13. Holton RA, Somoza C, Kim HB, Liang F, Biediger RJ, et al. First total synthesis of taxol. 1. Functionalization of the B ring. J Am Chem. Soc 1994;116:1597-60.
14. Holton R.A., Biediger R.J., Boatman P.D. Semisynthesis of taxol and taxotere. Suffness M. Taxol science and applications . 1995;3-25 CRC, Boca Raton, FL.
15. Hanson R.L., Wasylyk J.M., Nanduri V.B., Cazzulino D.L., Patel R.N., et al. Site-specific enzymatic hydrolysis of taxanes at C-10 and C-13. J Biol Chem. 35:1994;22145-22149.
16. Hanson RL, Patel RN, Szarka LJ. US Patent 5516676, 1996.
17. Hanson RL, Patel RN, Szarka LJ. US Patent 5523219, 1996.
18. Patel R.N. Tour de paclitaxel biocatalysis for semisynthesis . Annu Rev Microbiol. 98:1998;361-395.
19. Nanduri V.B., Hanson R.L., LaPorte T.L., Ko R., Patel R.N., et al. Fermentation and Isolation of C-10 deacetylase for the production of 10- DAB from baccatin III. Biotech Bioeng. 48:1995;547-550.
20. Hanson R.L., Howell J.M., Brzozowski B.D., Sullivan S.A., Patel R.N., et al. Enzymatic hydrolysis of 7-xylosyltaxanes by xylosidase from Moraxella sp. Biotechnol Appc Biochem. 26:1997;152-158.
21. Gueritte-Voegelein F., Senilh V., David B., Guenard D., Potier P. Chemical studies of 10-deacetyl baccatin III. Henisynthesis of taxol derivatives. Tetrahedron. 42:1986;4451-4455.
22. Magri N.F., Kingston D.G.I., Jitrangsri C., Piccareillo T. Modified taxol III. Preparation and acylation of baccatin III. J Org Chem. 51:1989;3239-3242.
23. Lee D, Kim K-C, Kim M-J. Selective enzymatic acylation of 10-deacetylbaccatin III. Tetrahedrom Lett 1998;39:9093-9042.
24. Patel R.N., Banerjee A., Howell J.M., McNamee C.G., Brzozowski D., et al. Microbial synthesis of (2R, 3S)-(-)-N-benzoyl-3-phenyl isoserine ethyl ester-a taxol side-chain synthon. Tetrahedron: Asymmetry. 4:1993;2069-2084.
25. Patel R.N., Banerjee A., Ko R., Howell J.M., Li W.-S., et al. Enzymatic preparation of (3R-cis)-3-(acetyloxy)-4-phenyl-2-azetidinone a taxol side- chain synthon . Biotechnol. Appl. Biochem. 20:1994;23-33.
26. Patel RN, Banerjee A, McNamme CG, Thottathil JK, Szarka LJ. US Patent 5420337, 1995.
27. Patel RN, Szarka LJ, Partyka R. US Patent 5567614, 1996.