Taxol biosynthesis: Molecular cloning and characterization of a cytochrome P450 taxoid 7β-hydroxylase

Chemistry and Biology

Volumn 11, Issue 5, 2004, Pages 663-672

  Chau, MyDoanh ^a   Jennewein, Stefan ^a,b   Walker, Kevin ^a,c   Croteau, Rodney ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

^b DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^c MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYTOCHROME P450; MIXED FUNCTION OXIDASE; PACLITAXEL;

ARTICLE; BIOSYNTHESIS; CHEMISTRY; GENETICS; METABOLISM; MOLECULAR CLONING; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; SEQUENCE ALIGNMENT;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BASE SEQUENCE; CLONING, MOLECULAR; CYTOCHROME P-450 ENZYME SYSTEM; MIXED FUNCTION OXYGENASES; MOLECULAR SEQUENCE DATA; PACLITAXEL; SEQUENCE ALIGNMENT;

TAXUS;

EID: 2642550828     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2004.02.025     Document Type: Article

References (49)

1. Wall M.E., Wani M.C. Paclitaxel. from discovery to clinic ACS Symp. Ser. 583:1995;18-30
2. Goldspiel B.R. Clinical overview of the taxanes. Pharmacotherapy. 17:1997;110S-125S
3. Skeel R.T. Antineoplastic drugs and biological response modifiers. Classification, use, and toxicity of clinically useful agents. Fifth Edition R.T., Skeel Handbook of Chemotherapy. 1999;63-144 Lippincott, Williams & Wilkins, Baltimore, MD
4. Suffness M. Overview of paclitaxel research. progress on many fronts ACS Symp. Ser. 583:1995;1-17
5. Kingston D.G.I., Jagtop P.G., Yuan H., Samala L. The chemistry of Taxol and related taxoids. Fortschr. Chem. Org. Naturst. 84:2002;53-225
6. Holton R.A., Biediger R.J., Boatman P.D. Semisynthesis of Taxol and Taxotere. Suffness M. Taxol. Science and Applications:1995;97-121 CRC Press, Boca Raton, FL
7. Cragg G.M., Schepartz S.A., Suffness M., Grever M.R. The Taxol supply crisis. New NCI policies for handling the large-scale production of novel natural product anticancer and anti-HIV agents. J. Nat. Prod. 56:1993;1657-1668
8. Ketchum R.E.B., Gibson D.M. Paclitaxel production in cell suspension cultures of Taxus. Plant Cell Tissue Organ Cult. 46:1996;9-16
9. Yukimune Y., Tabata H., Higashi H., Hara Y. Methyl jasmonate-induced overproduction of paclitaxel and baccatin III in Taxus cell suspension cultures. Nat. Biotechnol. 14:1996;1129-1132
10. Hefner J., Ketchum R.E.B., Croteau R. Cloning and functional expression of a cDNA encoding geranylgeranyl diphosphate synthase from Taxus canadensis and assessment of the role of this prenyltransferase in cells induced for Taxol production. Arch. Biochem. Biophys. 360:1998;62-74
11. Koepp A.E., Hezari M., Zajicek J., Vogel B.S., LaFever R.E., Lewis N.G., Croteau R. Cyclization of geranylgeranyl diphosphate to taxa-4(5), 11(12)-diene is the committed step of Taxol biosynthesis in Pacific yew. J. Biol. Chem. 270:1995;8686-8690
12. Hezari M., Lewis N.G., Croteau R. Purification and characterization of taxa-4(5), 11(12)-diene synthase from Pacific yew (Taxus brevifolia) that catalyzes the first committed step of Taxol biosynthesis. Arch. Biochem. Biophys. 322:1995;437-444
13. Jennewein S., Croteau R. Taxol. biosynthesis, molecular genetics and biotechnological applications Appl. Microbiol. Biotechnol. 57:2001;13-19
14. Walker K.D., Croteau R. Taxol biosynthetic genes. Phytochemistry. 58:2001;1-7
15. Floss H.G., Mocek U. Biosynthesis of Taxol. Suffness M. Taxol. Science and Applications:1995;191-208 CRC Press, New York
16. Hefner J., Rubenstein S.M., Ketchum R.E.B., Gibson D.M., Williams R.M., Croteau R. Cytochrome P450-catalyzed hydroxylation of taxa-4(5), 11(12)-diene to taxa-4(20), 11(12)-dien-5α-ol. the first oxygenation step in Taxol biosynthesis Chem. Biol. 3:1996;479-489
17. Lovy Wheeler A., Long R.M., Ketchum R.E.B., Rithner C.D., Williams R.M., Croteau R. Taxol biosynthesis. differential transformations of taxadien-5α-ol and its acetate ester by cytochrome P450 hydroxylases from Taxus suspension cells Arch. Biochem. Biophys. 390:2001;265-278
18. Walker K., Fujisaki S., Long R., Croteau R. Molecular cloning and heterologous expression of the C-13 phenylpropanoid side chain-CoA acyltransferase that functions in Taxol biosynthesis. Proc. Natl. Acad. Sci. USA. 99:2002;12715-12720
19. Croteau R., Kutchan T.M., Lewis N.G. Natural products (secondary metabolism). Buchanan B.B., Gruissem W., Jones R.L. Biochemistry and Molecular Biology of Plants. 2000;1250-1318 American Society of Plant Physiology, Rockville, MD
20. Wildung M.R., Croteau R. A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of Taxol biosynthesis. J. Biol. Chem. 271:1996;9201-9204
21. Walker K., Schoendorf A., Croteau R. Molecular cloning of a taxa-4(20), 11(12)-dien-5α-ol-O-acetyl transferase cDNA from Taxus and functional expression in Escherichia coli. Arch. Biochem. Biophys. 374:2000;371-380
22. Walker K., Croteau R. Molecular cloning of a 10-deacetylbaccatin III-10-O-acetyl transferase cDNA from Taxus and functional expression in Escherichia coli. Proc. Natl. Acad. Sci. USA. 97:2000;583-587
23. Walker K., Croteau R. Taxol biosynthesis. molecular cloning of a benzoyl CoA: taxane-2α-O-benzoyl transferase cDNA from Taxus and functional expression in Escherichia coli Proc. Natl. Acad. Sci. USA. 97:2000;13591-13596
24. Walker K., Long R., Croteau R. The final acylation step in Taxol biosynthesis. cloning of the taxoid C13-side-chain N-benzoyltransferase from Taxus Proc. Natl. Acad. Sci. USA. 99:2002;9166-9171
25. Ketchum R.E.B., Gibson D.M., Croteau R.B., Shuler M.L. The kinetics of taxoid accumulation in cell suspension cultures of Taxus following elicitation with methyl jasmonate. Biotechnol. Bioeng. 62:1999;97-105
26. Schoendorf A., Rithner C.D., Williams R.M., Croteau R. Molecular cloning of a cytochrome P450 taxane 10β-hydroxylase cDNA from Taxus and functional expression in yeast. Proc. Natl. Acad. Sci. USA. 98:2001;1501-1506
27. Jennewein S., Long R.M., Williams R.M., Croteau R. Cloning and characterization of taxadiene 5α-hydroxylase, a mechanistically unusual cytochrome P450 monooxygenase which catalyzes the first oxygenation step of Taxol biosynthesis. Chem. Biol. 11:2003;379-387
28. Jennewein S., Rithner C.D., Williams R.M., Croteau R. Taxol biosynthesis. taxane 13α-hydroxylase is a cytochrome P450-dependent monooxygenase Proc. Natl. Acad. Sci. USA. 98:2001;13595-13600
29. Jennewein S., Rithner C.D., Williams R.M., Croteau R. Taxoid metabolism. taxoid 14β-hydroxylase is a cytochrome P450-dependent monooxygenase Arch. Biochem. Biophys. 413:2003;262-270
30. Miyazaki M., Shimizu K., Mishima H., Kurabayashi M. The constituents of the heartwood of Taxus cuspidata Sieb. et Zucc. Chem. Pharm. Bull. (Tokyo). 16:1968;546-548
31. Della Casa de Marcano, D.P., and Halsall, T.G. (1969). The isolation of seven new taxane derivatives from the heartwood of yew (Taxus baccata L.). Chem. Commun., 1282-1283.
32. Ketchum R.E.B., Rithner C.D., Qiu D., Kim Y.S., Williams R.M., Croteau R.B. Taxus metabolomics. methyl jasmonate preferentially induces production of taxoids oxygenated at C-13 in Taxus x media cell cultures Phytochemistry. 62:2003;901-909
33. Baloglu E., Kingston D.G.I. The taxane diterpenoids. J. Nat. Prod. 62:1999;1448-1472
34. Pompon D., Louerat B., Bronine A., Urban P. Yeast expression of animal and plant P450s in optimized redox environments. Methods Enzymol. 272:1996;51-64
35. Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 239:1964;2370-2378
36. Kingston D.G.I., Molinero A.A., Rimoldi J.M. The taxane diterpenoids. Fortschr. Chem. Org. Naturst. 61:1993;1-206
37. Chu A., Davin L.B., Zajicek J., Lewis N.G., Croteau R.B. Intramolecular acyl migrations in taxanes from Taxus brevifolia. Phytochemistry. 34:1993;473-476
38. von Wachenfeldt C., Johnson E.F. Structures of eukaryotic cytochrome P450 enzymes. Mechanism, Biochemistry Second Edition, Ortiz de Montellano P.R. Cytochrome P450. Structure:1995;183-223 Plenum, New York
39. Schenkman J.B., Jansson I. Spectral analysis of cytochrome P450. Methods Mol. Biol. 107:1998;25-33. (Cytochrome P450 Protocols)
40. Chaudhary A.G., Rimoldi J.M., Kingston D.G.I. Modified Taxols. 10. Preparation of. 7-deoxytaxol:1993;. J. Org. Chem. 58, 3798-3799.a highly bioactive Taxol derivative and interconversion of Taxol and epi-Taxol
41. Georg G.I., Harriman G.C.B. Taxol photoaffinity label. 7-(p)-azidobenzoyl)taxol synthesis and biological evaluation Bioorg. Med. Chem. Lett. 2:1992;735-738
42. Rimoldi J.M., Kingston D.G.I., Chaudhary A.G., Samaranayake G., Grover S., Hamel E. Modified Taxols. 9. Synthesis and biological evaluation of. 7-substituted(photoaffinity analogues of Taxol. J. Nat. Prod. 56):1993;1313-1330
43. Wu Q., Bounaud P.-Y., Kuduk S.D., Yang C.-P., Ojima I., Horwitz S.B., Orr G. Identification of the domains of photoincorporation of the 3′ and 7′-benzophenone analogues of Taxol in the carboxyl-terminal half of murine mdr1b P-glycoprotein. Biochemistry. 37:1998;11272-11279
44. Vyas D.M., Ueda Y., Wong H., Matiskella J.D., Hauck S., Mikkilineni A.B., Farina V., Rose W.C., Casazza A.M. Phosphatase-activated prodrugs of paclitaxel. ACS Symp. Ser. 583:1995;124-137
45. Ueda Y., Mikkilineni A.B., Knipe J.O., Rose W.C., Casazza A.M., Vyas D.M. Novel water soluble phosphate prodrugs of Taxol possessing in vivo antitumor activity. Bioorg. Med. Chem. Lett. 3:1993;1761-1766
46. Altstadt T.J., Fairchild C.R., Golik J., Johnston K.A., Kadow J.F., Lee F.Y., Long B.H., Rose W.C., Vyas D.M., Wong H., et al. Synthesis and antitumor activity of novel C-7 paclitaxel ethers. discovery of BMS-184476 J. Med. Chem. 44:2001;4577-4583
47. Rubenstein S.M., Vázquez A., Sansez-Cervara J.F., Williams R.M. Synthesis of stable and radioisotopomers of taxa-4(5), 11(12)-diene, taxa-4(20), 11(12)-diene and taxa-4(20), 11(12)-dien-5-α-ol, early intermediates in Taxol biosynthesis. J. Labelled Comp. Radiopharm. 43:2000;481-491
48. Paquette L.A., Wang H.-L., Su Z., Zhao M. Enantiospecific total synthesis of natural (+)-taxusin. 2. Functionalization of the A-ring and arrival at the target. J. Am. Chem. Soc. 120:1998;5213-5225
49. Bebernitz G.R., Dain J.G., Deems R.O., Otero D.A., Simpson W.R., Strohschein R.J. Reduction in glucose levels in STZ diabetic rats by 4-(2, 2-dimethyl-1-oxopropyl)benzoic acid. a prodrug approach for targeting the liver J. Med. Chem. 44:2001;512-523