526
Views
44
CrossRef citations to date
0
Altmetric
Original Articles

Cloning of a Gene Cluster Responsible for the Biosynthesis of Diterpene Aphidicolin, a Specific Inhibitor of DNA Polymerase α

, , , , , , , , & show all
Pages 146-152 | Received 23 Jul 2003, Accepted 10 Sep 2003, Published online: 22 May 2014

  • 1) Dalziel, W., Hesp, B., Stevenson, K. M., and Jarvis, J. A. J., The structure and absolute configuration of the antibiotic aphidicolin: a tetracyclic diterpenoid containing a new ring system. J. Chem. Soc. Perkin Trans. I, 2841–2851 (1973).
  • 2) Ikegami, S., Taguchi, T., Ohashi, M., Oguro, M., Nagano, H., and Mano, Y., Aphidicolin prevents mitotic cell division by interfering with the activity of DNA polymerase α. Nature, 275, 458–460 (1978).
  • 3) Feher, Z., and Mishra, N. C., An aphidicolin-resistant mutant of Chinese hamster ovary cell with altered DNA polymerase and 3′ exonuclease activities. Biochim. Biophys. Acta, 1263, 141–146 (1995).
  • 4) Toyota, M., and Ihara, M., Total synthesis of aphidicolanes and stemodanes. Tetrahedron, 55, 5641–5679 (1999).
  • 5) Oikawa, H., Ohashi, S., Ichihara, A., and Sakamura, S., Biosynthesis of diterpenoid aphidicolin: isolation of intermediates from P-450 inhibitor treated mycelia of Phoma betae. Tetrahedron, 55, 7541–7554 (1999).
  • 6) Oikawa, H., Ichihara, A., and Sakamura, S., The later stage of the biosynthesis of aphidicolin: accumulation of intermediates with cytochrome P-450 inhibitors. Agric. Biol. Chem., 53, 299–300 (1989).
  • 7) Oikawa, H., Toyomasu, T., Toshima, H., Ohashi, S., Kawaide, H., Kamiya, H., Ohtsuka, M., Shinoda, S., Mitsuhashi, W., and Sassa, T., Cloning and functional expression of cDNA encoding aphidicolan-16β-ol synthase: a key enzyme responsible for formation of an unusual diterpene skeleton in biosynthesis of DNA polymerase α inhibitor aphidicolin. J. Am. Chem. Soc., 123, 5154–5155 (2001).
  • 8) Toshima, H., Oikawa, H., Yada, H., Ono, H., Toyomasu, T., and Sassa, T., Total synthesis of (±)-syn-copalol. Biosci. Biotechnol. Biochem., 65, 2504–2510 (2002).
  • 9) Oikawa, H., Nakamura, K., Toshima, H., Toyomasu, T., and Sassa, T., Proposed mechanism for the reaction catalyzed by a diterpene cyclase, aphidicolan-16β-ol synthase: experimental results on biomimetic cyclization and examination of the cyclization pathway by ab initio calculations. J. Am. Chem. Soc., 124, 9145–9153 (2002).
  • 10) Bullock, W. O., Fernandez, J. M., and Short, J. M., XL1-Blue: a high-efficiency plasmid transforming recA Escherichia coli strain with β-galactosidase selection. Biotechniques, 5, 376–378 (1987).
  • 11) Ausubel, F. M., Brent, R., Kingston, R. E., Moore, D. D., Seiden, J. G., Smith, J. A., and Struhl, K., Current protocols in molecular biology, Wiley, New York (1987).
  • 12) Sambrook, J., and Russell, D. W., Molecular cloning: a laboratory manual, 3rd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York (2001).
  • 13) Toyomasu, T., Kawaide, H., Mitsuhashi, W., Inoue, Y., and Kamiya, Y., Phytochrome regulates gibberellin biosynthesis during germination of photoblastic lettuce seeds. Plant Physiol., 118, 1517–1523 (1998).
  • 14) Sanger, F., Nicklen, S., and Coulson, A. R., DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. USA, 74, 5463–5467 (1977).
  • 15) Barton, D., Nakanishi, K., and Meth-Cohn, O., Comprehensive natural products chemistry, vol. 1: Polyketides and other secondary metabolites including fatty acids and their derivatives, Elsevier, Amsterdam (1999).
  • 16) Keller, N. P., and Hohn, T. M., Metabolic pathway gene clusters in filamentous fungi. Fung. Genet. Biol., 21, 17–29 (1996).
  • 17) Tudzynski, B., Biosynthesis of gibberellins in Gibberella fujikuroi: biomolecular aspects. Appl. Microbiol. Biotechnol., 52, 298–310 (1999).
  • 18) Oikawa, H., Sassa, T., and Toyomasu, T., Aphidicolin biosynthetic gene cluster. Patent PCT WO 03/000902 A1 (Jan. 3, 2003).
  • 19) von Wachenfekdt, C., and Johnson, E. F., Structures of eukaryotic cytochrome P450 enzymes. In “Cytochrome P-450 Structure, Mechanism and Biochemistry” 2nd ed., ed. Ortiz de Montellano, P. R., Plenum Press, New York, pp. 183–223 (1995).
  • 20) Brown, D. W., Yu, J. H., Kelkar, H. S., Fernandes, M., Nesbitt, T. C., Keller, N. P., Adams, T. H., and Leonard, T. J., Twenty-five coregulated transcripts define a sterigmatocystin gene cluster in Aspergillus nidulans. Proc. Natl. Acad. Sci. USA, 93, 1418–1422 (1996).
  • 21) Tudzynski, B., and Holter, K., Gibberellin biosynthetic pathway in Gibberella fujikuroi: evidence for a gene cluster. Fung. Genet. Biol., 25, 157–170 (1998).
  • 22) Alexander, N. J., Hohn, T. M., and McCormick, S. P., The TRI11 gene of Fusarium sporotrichioides encodes a cytochrome P-450 monooxygenase required for C-15 hydroxylation in trichothecene biosynthesis. Appl. Environ. Microbiol., 64, 221–225 (1998).
  • 23) Prieto, R., Yousibova, G. L., and Woloshuk, C. P., Identification of aflatoxin biosynthesis genes by genetic complementation in an Aspergillus flavus mutant lacking the aflatoxin gene cluster. Appl. Environ. Microbiol., 62, 3567–3571 (1996).
  • 24) Rojas, M. C., Hedden, P., Gaskin, P., and Tudzynski, B., The P450-1 gene of Gibberella fujikuroi encodes a multifunctional enzyme in gibberellin biosynthesis. Proc. Natl. Acad. Sci. USA, 98, 5838–5843 (2001).
  • 25) Cary, J. W., Dyer, J. M., Ehrlich, K. C., Wright, M. S., Liang, S. H., and Linz, J. E., Molecular and functional characterization of a second copy of the aflatoxin regulatory gene, aflR-2, from Aspergillus parasiticus. Biochim. Biophys. Acta, 1576, 316–323 (2002).
  • 26) Pitkin, J. W., Panaccione, D. G., and Walton, J. D., A putative cyclic peptide efflux pump encoded by the TOXA gene of the plant-pathogenic fungus Cochliobolus carbonum. Microbiology, 142, 1557–1565 (1996).
  • 27) Vermeulen, T., Schoonbeek, H., and De Waard, M. A., The ABC transporter BcatrB from Botrytis cinerea is a determinant of the activity of the phenylpyrrole fungicide fludioxonil. Pest Manag. Sci., 57, 393–402 (2001).
  • 28) Paulsen, I. T., Brown, M. H., and Skurray, R. A., Proton-dependent multidrug efflux systems. Microbiol. Rev., 60, 575–608 (1996).
  • 29) Kuzuguchi, T., Morita, Y., Sagami, I., Sagami, H., and Ogura, K., Human geranylgeranyl diphosphate synthase. cDNA cloning and expression. J. Biol. Chem., 274, 5888–5894 (1999).
  • 30) Jiang, Y., Proteau, P., Poulter, D., and Ferro-Novick, S., BTS1 encodes a geranylgeranyl diphosphate synthase in Saccharomyces cerevisiae. J. Biol. Chem., 270, 21793–21799 (1995).
  • 31) Okada, K., Saito, T., Nakagawa, T., Kawamukai, M., and Kamiya, Y., Five geranylgeranyl diphosphate synthases expressed in different organs are localized into three subcellular compartments in Arabidopsis. Plant Physiol., 122, 1045–1056 (2000).
  • 32) Bohlmann, J., Meyer-Gauen, G., and Croteau, R., Plant terpenoid synthases: molecular biology and phylogenetic analysis. Proc. Natl. Acad. Sci. USA, 95, 4126–4133 (1998).
  • 33) Kawaide, H., Imai, R., Sassa, T., and Kamiya, Y., Ent-kaurene synthase from the fungus Phaeosphaeria sp. L487. cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase in fungal gibberellin biosynthesis. J. Biol. Chem., 272, 21706–21712 (1997).
  • 34) Toyomasu, T., Kawaide, H., Ishizaki, A., Shinoda, S., Otsuka, M., Mitsuhashi, W., and Sassa, T., Cloning of a full-length cDNA encoding ent-kaurene synthase from Gibberella fujikuroi: functional analysis of a bifunctional diterpene cyclase. Biosci. Biotechnol. Biochem., 64, 660–664 (2000).
  • 35) Misawa, N., Satomi, Y., Kondo, K., Yokoyama, A., Kajiwara, S., Saito, T., Ohtani, T., and Miki, W., Structure and functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin biosynthetic pathway proposed at the gene level. J. Bacteriol., 177, 6575–6584 (1995).
  • 36) Dairi, T., Hamano, Y., Kuzuyama, T., Itoh, N., Furihata, K., and Seto, H., Eubacterial diterpene cyclase genes essential for production of the isoprenoid antibiotic, terpentecin. J. Bacteriol., 183, 6085–6094 (2001).
  • 37) Young, C., McMillan, L., Telfer, E., and Scott, B., Molecular cloning and genetic analysis of an indole-diterpene gene cluster from Penicillium paxilli. Mol. Microbiol., 39, 754–764 (2001).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.