Molecular genetics of lovastatin and compactin biosynthesis

Handbook of Industrial Mycology

Volumn , Issue , 2004, Pages 479-492

  Hutchinson, C Richard ^a   Kennedy, Jonathan ^a   Park, Cheonseok ^b   Auclair, Karine ^c   Kendrew, Steven G ^d   Vederas, John ^e  

^a KOSAN BIOSCIENCES INC   (United States)

^b Kyung Hee University   (South Korea)

^c MCGILL UNIVERSITY   (Canada)

^d BIOTICA TECHNOLOGY LTD   (United Kingdom)

^e UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85015504297     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9780203970553     Document Type: Chapter

References (45)

1. O’Hagan, D. The Polyketide Metabolites Ellis Horwood. New York, 1991.
2. Rawlings, B.J. Biosynthesis of polyketides (other than actinomycete macrolides). Nat. Prod. Rep. 1999, 16, 425-484.
3. Igel, M.; Sudhop, T.; von Bergmann, K. Eur. J. Clin. Pharmacol. 2001, 57, 357-364.
4. Sutherland, A.; Auclair, K.; Vederas, J.C. Recent advances in the biosynthetic studies of lovastatin. Curr. Opin. Drug Discov. Develop. 2001, 4, 229-236.
5. Cane, D.E.; Walsh, C.T.; Khosla, C. Harnessing the biosynthetic code: combinations, permutations, and mutations. Science 1998, 282, 63-68.
6. Katz, L. Manipulation of modular polyketide synthases. Chem. Rev. 1997, 97, 2557-2575.
7. Staunton, J.; Wilkinson, B. Biosynthesis of erythromycin and rapamycin. Chem. Rev. 1997, 97, 2611-2629.
8. Donadio, S.; Staver, M.J.; McAlpine, J.B.; Swanson, S.J.; Katz, L. Modular organization of genes required for complex polyketide biosynthesis. Science 1991, 252, 675-679.
9. August, P.R.; Tang, L.; Yoon, Y.J.; Ning, S.; Muller, R.; Yu, T.W.; Taylor, M.; Hoffman, D.; Kim, C.G.; Zhang, X.; Hutchinson, C.R.; Floss, H.G. Biosynthesis of the ansamycin antibiotic rifamycin: deductions from the molecular analysis of rif biosynthetic gene cluster of Amycolatopsis mediterranei S699. Chem. Biol. 1998, 5, 69-79.
10. Schwecke, T.; Aparico, J.F.; Molnar, I.; Konig, A.; Khaw, L.E.; Haydock, S.F.; Oliynyk, M.; Caffrey, P.; Cortes, J.; Lester, J.B.; Bohm, G.A.; Staunton, J.; Leadlay, P.F. The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7839-7843.
11. Motamedi, H.; Cai, S.J.; Shafiee, A.; Elliston, K.O. Structural organization of a multifunctional polyketide synthase involved in the biosynthesis of the macrolide immunosuppressant FK506. Eur. J. Biochem. 1997, 244, 74-80.
12. Moore, R.N.; Bigam, G.; Chan, J.K.; Hogg, A.M.; Nakasima, T.T.; Vederas, J.C. Biosynthesis of the hypocholesterolemic agent mevinolin by Aspergillus terreus. Determination of the origin of carbon, hydrogen and oxygen atoms by 13C NMR and mass spectrometry. J. Am. Chem. Soc. 1985, 107, 3694-3701.
13. Wagschal, K.; Yoshizawa, Y.; Witter, D.J.; Liu, Y.; Vederas, J.C. Biosynthesis of ML-236C and the hypocholesterolemic agents compactin by Penicillium aurantiogriseus and lovastatin by Aspergillus terreus: determination of the origin of carbon, hydrogen and oxygen atoms by 13C NMR spectroscopy and observation of unusual labelling of acetate-derived oxygens by 18O2. J. Chem. Soc. Perkin Trans. I. 1996 2357-2363.
14. Endo, A.; Hasumi, K. Fungal Biotechnology. Anke, T., Ed. Chapman & Hall: Weinheim, 1997; (162-172).
15. Endo, A.; Hasumi, K. HMG-CoA reductase inhibitors. Nat. Prod. Rep. 1993 541-550.
16. Yamamoto, Y.; Hori, A.; Hutchinson, C.R. Biosynthesis of macrolide antibiotics. 6. Late steps in brefeldin A biosynthesis. J. Am. Chem. Soc. 1985, 107, 2471-2474.
17. Kono, Y.; Daly, J.M. Characterization of the host-specific pathotoxin produced by Helminthosporium maydis, race T, affecting corn with Texas male sterile cytoplasm. Bioorg. Chem. 1979, 8, 391-397.
18. Yang, G.; Rose, M.S.; Turgeon, B.G.; Yoder, O.C. A polyketide synthase is required for fungal virulence and production of the polyketide T-toxin. Plant Cell 1996, 8, 2139-2150.
19. Witter, D.J.; Vederas, J.S. Putative Diels-Alder-catalyzed cyclization during the biosynthesis of lovastatin. J. Org. Chem. 1996, 61, 2613-262.
20. Treiber, L.R.; Reamer, R.A.; Rooney, C.S.; Ramjit, H.G. Origin of monacolin L from Aspergillus terreus cultures. J. Antibiotics 1989, 42, 30-36.
21. Nakamura, T.; Komagata, D.; Murakawa, S.; Sakai, K.; Endo, A. Isolation and biosynthesis of 3[??]-hydroxy-3,5-dihydromonacolin J. J. Antibiotics 1990, 43, 1597-1600.
22. Abe, Y.; Suzuki, T.; Ono, C.; Iwamoto, K.; Hosobuchi, M.; Yoshikawa, H. Molecular cloning and characterization of an ML-236B (compactin) biosynthetic gene cluster in Penicillium citrinum. Molec. Gen. Genet. 2002, 267, 636-646.
23. Chan, L.K.; Moore, R.N.; Nakashima, T.; Vederas, J.S. Biosynthesis of mevinolin, spectral assignment by double quantum coherence NMR after high carbon-13 incorporation. J. Am. Chem. Soc. 1983, 105, 3334-3336.
24. Yoshizawa, Y.; Witter, D.J.; Liu, Y.; Vederas, J.C. Revision of the biosynthetic origin of oxygens in mevinolin (lovastatin), a hypocholesterolemic drug from Aspergillus terreus MF 4845. J. Am. Chem. Soc. 1994, 116, 2693-2694.
25. Auclair, K.; Sutherland, A.; Kennedy, J.; Witter, D.J.; Van den Heever, J.P.; Hutchinson, C.R.; Vederas, J.C. Lovastatin nonaketide synthase (LNKS) catalyzes an intramolecular Diels-Alder reaction of a substrate analog. J. Amer. Chem. Soc. 2000, 122, 11519-11520.
26. Hendrickson, L.; Davis, C.R.; Roach, C.; Nguyen, D.K.; Aldrich, T.; McAda, P.C.; Reeves, C.D. Lovastatin biosynthesis in Aspergillus terreus: characterization of blocked mutants, enzyme activities and a multifunctional polyketide synthase gene. Chem. Biol. 1999, 6, 429-439.
27. Konz, D.; Marahiel, M.A.? How do peptide synthetases generate structural diversity. Chem. Biol. 1999, 6, R39-R4.
28. Kennedy, J.; Auclair, K.; Kendrew, S.G.; Park, C.; Vederas, J.C.; Hutchinson, C.R. Modulation of polyketide synthase activity by accessory proteins during lovastatin biosynthesis. Science 1999, 284, 1368-1372.
29. Offenzeller, M.; Santer, G.; Totschnig, K.; Su, Z.; Moser, H.; Traber, R.; Schneider-Scherzer, E. Biosynthesis of the unusual amino acid (4R)-4-[(E)-2-buteny]-4-methyl-L-threonine of cyclosporin A: Enzymatic analysis of the reaction sequence including identification of the methylation precursor in a polyketide pathway. Biochemistry 1996, 35, 8401-8412.
30. Tang, L.; Shah, S.; Chung, L.; Carney, J.; Katz, L.; Khosla, C.; Julien, B. Cloning and heterologous expression of the epothilone gene cluster. Science 2000, 287, 640-2.
31. Molnar, I.; Schupp, T.; Ono, M.; Zirkle, R.; Milnamow, M.; Nowak-Thompson, B.; Engel, N.; Toupet, C.; Stratmann, A.; Cyr, D.D.; Gorlach, J.; Mayo, J.M.; Hu, A.; Goff, S.; Schmid, J.; Ligon, J.M. The biosynthetic gene cluster for the microtubule-stabilizing agents epothilones A and B from Sorangium cellulosum Soce90. Chem. Biol. 2000, 7, 97-109.
32. Sorensen, J.L.; Auclair, K.; Kennedy, J.; Hutchinson, C.R.; Vederas, J.C. Transformations of cyclic nonaketides by Aspergillus terreus mutants blocked for lovastatin biosynthesis at the lovA and lovC genes. Organic Biomolec. Chem., in press. 2002.
33. Auclair, K.; Kennedy, J.; Hutchinson, C.R.; Vederas, J.C. Conversion of cyclic nonaketides to lovastatin and compactin by a lovC deficient mutant of Aspergillus terreus. Bioorg. Med. Chem. Lett. 2001, 11, 1527-1531.
34. Todd, R.B.; Andrianopoulos, A. Evolution of a fungal regulatory gene family: The Zn(II)2Cys6 binuclear cluster DNA binding motif. Fungal Genet. Biol. 1997, 21, 388-405.
35. Keller, N.P.; Hohn, T.M. Metabolic pathway gene clusters in filamentous fungi. Fungal Genet. Biol. 1997, 21, 17-29.
36. Bochar, D.A.; Stauffacher, C.V.; Rodwell, V.W. Sequence comparisons reveal two classes of 3-hydroxy-3-methylglutaryl coenzyme A reductase. Molec. Genet. Metab. 1999, 66, 122-127.
37. Hutchinson, C.R.; Kennedy, J.; Park, C.; Kendrew, S.; Auclair, K.; Vederas, J.C. Aspects of the biosynthesis of non-aromatic fungal polyketides by iterative polyketide synthases. Antonie Van Leeuwen 2000, 78, 287-295.
38. Pitkin, J.W.; Panaccione, D.G.; Walton, J.D. A putative cyclic peptide efflux pump encoded by the TOXA gene of the plant-pathogenic fungus Cochliobolus carbonum. Microbiology 1996, 142, 1557-1565.
39. Ichihara, A.; Oikawa, H. Diels-Alder type natural products. Structures and biosynthesis. Curr. Org. Chem. 1998, 2, 365-394.
40. Katayama, K.; Kobayashi, T.; Oikawa, H.; Honma, M.; Ichihara, A. Enzymatic activity and partial purification of solanapyrone synthase: first enzyme catalyzing Diels-Alder reaction. Biochem. Biophys. Acta. 1998, 1384, 387-395.
41. Watanabe, K.; Mie, T.; Ichihara, A.; Oikawa, H.; Honma, M. Detailed reaction mechanism of macrophomate synthase. Extraordinary enzyme catalyzing five-step transformation from 2- pyrones to benzoates. J Biol Chem. 2000, 275, 38393-38401.
42. Smith, S. The animal fatty acid synthase: One gene, one polypeptide, seven enzymes. FASEB. J. 1994, 8, 1248-1259.
43. Wiesner, P.; Beck, J.; Beck, K.F.; Ripka, S.; Muller, G.; Lucke, S.; Schweizer, E. Isolation and sequence analysis of the fatty acid synthetase FAS2 gene from Penicillium patulum. Eur. J. Biochem. 1998, 177, 69-79.
44. Vinci, V.A.; Conder, M.J.; McAda, P.C.; Reeves, C.D.; Rambosek, J.; Davis, C.R.; Hendrickson, L.E. DNA encoding triol polyketide synthase. U.S.5 1998, 744, 350.
45. Abe, Y.; Suzuki, T.; Mizuno, T.; Ono, C.; Iwamoto, K.; Hosobuchi, M.; Yoshikawa, H. Effect of increased dosage of the ML-236B (compactin) biosynthetic gene cluster on ML 236B production in Penicillium citrinum. Mol. Genet. Genomics 2002, 268, 130-137.