Cloning of a gene cluster encoding enzymes responsible for the mevalonate pathway from a terpenoid-antibiotic-producing Streptomyces strain

Bioscience, Biotechnology and Biochemistry

Volumn 65, Issue 7, 2001, Pages 1627-1635

  Hamano, Yoshimitsu ^a   Dairi, Tohru ^a   Yamamoto, Masahiro ^a   Kawasaki, Takashi ^a   Kaneda, Kazuhide ^b   Kuzuyama, Tomohisa ^b   Itoh, Nobuya ^a   Seto, Haruo ^b  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

Gene cloning; Mevalonate pathway; Streptomyces; Terpenoid; Terpentecin

Indexed keywords

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; KITASATOSPORA GRISEOLA; STREPTOMYCES; STREPTOMYCES LIVIDANS;

ANTIINFECTIVE AGENT; CARBOXYLYASE; DIPHOSPHOMEVALONATE DECARBOXYLASE; DITERPENE; FARNESYL TRANS TRANSFERASE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE; HYDROXYMETHYLGLUTARYL COENZYME A SYNTHASE; ISOMERASE; ISOPENTENYL DIPHOSPHATE DELTA ISOMERASE; ISOPENTENYLDIPHOSPHATE DELTA-ISOMERASE; MEVALONATE KINASE; MEVALONIC ACID; PHOSPHOMEVALONATE KINASE; PHOSPHOTRANSFERASE; RECOMBINANT PROTEIN; TERPENTECIN; TRANSFERASE;

ARTICLE; BACTERIAL GENE; BIOSYNTHESIS; ENZYMOLOGY; ESCHERICHIA COLI; GENE EXPRESSION; GENETICS; METABOLISM; MOLECULAR CLONING; MULTIGENE FAMILY; STREPTOMYCES;

ALKYL AND ARYL TRANSFERASES; ANTI-BACTERIAL AGENTS; CARBON-CARBON DOUBLE BOND ISOMERASES; CARBOXY-LYASES; CLONING, MOLECULAR; DITERPENES; ESCHERICHIA COLI; FARNESYLTRANSTRANSFERASE; GENE EXPRESSION; GENES, BACTERIAL; HYDROXYMETHYLGLUTARYL COA REDUCTASES; HYDROXYMETHYLGLUTARYL-COA SYNTHASE; MEVALONIC ACID; MULTIGENE FAMILY; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); PHOSPHOTRANSFERASES (PHOSPHATE GROUP ACCEPTOR); RECOMBINANT PROTEINS; STREPTOMYCES;

EID: 0035408665     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.65.1627     Document Type: Article

References (42)

1. Porter, J. W. and Spurgeon, S. L., Biosynthesis of isoprenoid compounds, vol. 1. John Wiley & Sons, Inc., New York (1981).
2. Porter, J. W. and Spurgeon, S. L., Biosynthesis of isoprenoid compounds, vol. 1. John Wiley & Sons, Inc., New York (1983).
3. Servouse, M., Mons, N., Baillaargeat, J. L., and Karst, F., Isolation and characterization of yeast mutants blocked in mevalonic acid formation. Biochem. Biophy. Res. Com., 123, 424-430 (1984).
4. Chappell, J., Biochemistry and molecular biology of the isoprenoid biosynthetic pathways in plants. Annu. Rev. Plant. Physiol. Plant. Mol. Biol., 46, 521-547 (1995).
5. Horbach, S., Sahm, H., and Welle, R., Isoprenoid biosynthesis in bacteria: Two different pathways? FEMS Microbiol. Lett., 111, 135-140 (1993).
6. Rohmer, M., Knani, M., Simonin, P., Sutter, B., and Sahm, H., Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem. J., 295, 517-524 (1993).
7. Rohmer, M., Seemann, M., Horbach, S., Bringer-Meyer, S., and Sahm, H., Glyceraldehyde 3-phosphate and pyruvate as precursors of isoprenic units in an alternative non-mevalonate pathway for terpenoid biosynthesis. J. Am. Chem. Soc., 118, 2564-2566 (1996).
8. Sprenger, G. A., Schorken, U., Wiegert, T., Grolle, S., DeGraaf, A. A., Taylor, S. V., Begley, T. P., Bringer-Meyer, S., and Sahm, H., Identification of a thiamin-dependent synthase in Escherichia coli required for the formation of the 1-deoxy-D-xylulose 5-phosphate precursor to isoprenoids, thiamin, and pyridoxol. Proc. Natl. Acad. Sci. USA, 94, 12857-12862 (1997).
9. Lois, L. M., Campos, N., Rosa Putra, S., Danielsen, K., Rohmer, M., and Boronat, A., Cloning and characterization of a gene from Escherichia coli encoding a transketolase-like enzyme that catalyzes the synthesis of D-1-deoxyxylulose 5-phosphate, a common precursor for isoprenoid, thiamin, and pyridoxol biosynthesis. Proc. Natl. Acad. Sci. USA, 95, 2105-2110 (1998).
10. Takahashi, S., Kuzuyama, T., Watanabe, H., and Seto, H., A 1-deoxy-D-xylulose 5-phosphate reductoisomerase catalyzing the formation of 2-C-methyl-D-erythritol 4-phosphate in an alternative nonmevalonate pathway for terpenoid biosynthesis. Proc. Natl. Acad. Sci. USA, 95, 9879-9884 (1998).
11. Rohdich, F., Wungsintaweekul, J., Fellermeier, M., Sagner, S., Herz, S., Kis, K., Eisenreich, W., Bacher, A., and Zenk, M. H., Cytidine 5′-triphosphate-dependent biosynthesis of isoprenoids: YgbP protein of Escherichia coli catalyzes the formation of 4-diphosphocytidyl-2-C-methylerythritol. Proc. Natl. Aca. Sci. USA, 95, 11758-11763 (1999).
12. Lüttgen, H., Rohdich, F., Herz, S., Wungsintaweekul, J., Hecht, S., Schuhr, C. A., Fellermeier, M., Sagner, S., Zenk, M. H., Bacher, A., and Eisenreich, W., Biosynthesis of terpenoids: YchB protein of Escherichia coli phosphorylates the 2-hydroxy group of 4-phosphocytidyl-2-C-methyl-D-erythritol. Proc. Natl. Acad. Sci. USA, 97, 1062-1067 (2000).
13. Herz, S., Wungsintaweekul, J., Schuhr, C. A., Hecht, S., Lüttgen, H., Sagner, S., Fellermeier, M., Eisenreich, W., Zenk, M. H., Bacher, A., and Rohdich, F., Biosynthesis of terpenoid: YgbB protein converts 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate to 2-C-methyl-D-erythritol 2, 4-cyclodiphosphate. Proc. Natl. Acad. Sci. USA, 97, 2486-2490 (2000).
14. Kuzuyama, T., Takagi, M., Kaneda, K., Dairi, T., and Seto, H., Formation of 4-(cytidine 5′-diphospho)-2-C-methyl-D-erythritol from 2-C-methyl-D-erythritol 4-phosphate by 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, a new enzyme in the nonmevalonate pathway. Tetrahedron Lett., 41, 703-706 (2000).
15. Kuzuyama, T., Takagi, M., Kaneda, K., Watanabe, H., Dairi, T., and Seto, H., Studies on the nonmevalonate pathway: Conversion of 4-(cytidine 5′-diphospho)-2-C-methyl-D-erythritol to its 2-phospho derivative by 4-(cytidine 5′-diphospho)-2-C-methyl-D-erythritol kinase. Tetrahedron Lett., 41, 2925-2928 (2000).
16. Kuzuyama, T., Takagi, M., Kaneda, K., Watanabe, H., Dairi, T., and Seto, H., Studies on the nonmevalonate pathway: Formation of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate from 2-phospho-4-(cytidine 5′-diphospho)-2-C-methyl-D-erythritol. Tetrahedron Lett., 41, 3395-3398 (2000).
17. Seto, H., Watanabe, H., and Furihata, K., Simultaneous operation of the mevalonate and nonmevalonate pathways in the biosynthesis of isopentenyl diphosphate in Streptomyces aeriouvifer. Tetrahedron Lett., 37, 7979-7982 (1996).
18. Takahashi, S., Kuzuyama, T., and Seto, H., Purification, characterization, and cloning of a eubacterial 3-hydroxy-3-methylglutaryl coenzyme A reductase, a key enzyme involved in biosynthesis of terpenoids. J. Bacteriol., 181, 1256-1263 (1999).
19. Takagi, M., Kuzuyama, T., Takahashi, S., and Seto, H., A gene cluster for the mevalonate pathway from Streptomyces sp. strain CL190. J. Bacteriol., 182, 4153-4157 (2000).
20. Dairi, T., Motohira, Y., Kuzuyama, T., Takahashi, S., Itoh, N., and Seto, H., Cloning of the gene encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase from terpenoid antibiotics-producing Streptomyces strains. Mol. Gen. Genet., 262, 957-964 (2000).
21. Isshiki, K., Tamamura, T., Sawa, T., Naganawa, H., Takeuchi, T., and Umezawa, H., Biosynthetic studies of terpentecin. J. Antibiot., 34, 1634-1635 (1986).
22. Tamamura, T., Sawa, T., Isshiki, K., Masuda, T., Homma, Y., Iinuma, H., Naganawa, H., Hamada, M., Takeuchi, T., and Umezawa, H., Isolation and characterization of terpentecin, a new antitumor antibiotic. J. Antibiot., 38, 1664-1669 (1985).
23. Kuzuyama, T., Takahashi, S., and Seto, H., Construction and characterization of Escherichia coli disruptants defective in the yaeM gene. Biosci. Biotechnol. Biochem., 63, 776-778 (1999).
24. Hopwood, D. A., Bibb, M. J., Chater, K. F., Kieser, T., Bruton, C. J., Kieser, H. M., Lydiate, D. J., Smith, C. P., Ward, J. M., and Schremp, H., Gene manipulation of Streptomyces, a laboratory manual. The John Innes Foundation, Norwich, UK. (1985).
25. Vara, J., Lewandowska-Skarbek, M., Wang, Y. G., Donadio, S., and Hutchinson, C. R., Cloning of genes governing the deoxysugar portion of the erythromycin biosynthesis pathway in Saccharopolyspora erythraea (Streptomyces erythreus). J. Bacteriol., 171, 5872-5881 (1989).
26. Dairi, T., Ohta, T., Hashimoto, E., and Hasegawa, M., Organization and nature of fortimicin A (astromicin) biosynthetic genes studied using a cosmid library of Micromonospora olivasterospora DNA. Mol. Gen. Genet., 236, 39-48 (1992).
27. Maniatis, T., Fritsch, E. F., and Sambrook, J., Molecular cloning: a laboratory manual, Cold Spring Harbor Laboratory, Cold Spring Harbor, New York (1982).
28. Sanger, F., Nicklen, S., and Coulson, A. R., DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. USA, 74, 5463-5467 (1977).
29. Bibb, M. J., Jansen, G. R., and Ward, J. M., Cloning and analysis of the promoter of the erythromycin resistance gene (ermE) of Streptomyces erythraeus. Gene, 38, 215-226 (1985).
30. Schmitt-John, T. and Engels, J. W., Promoter constructions for efficient secretion expression in Sireptomyces lividans. Appl. Microbiol. Biotechnol., 36, 493-498 (1992).
31. Bibb, M. J., White, J., Ward, J. M., and Jansen, G. R., The mRNA for the 23S rRNA methylase encoded by the ermE gene of Saccharopolyspora erythraea is translated in the absence of a conventional ribosome-binding site. Mol. Microbiol., 14, 533-545 (1994).
32. Ohto, C., Ishida, C., Koike-Takeshita, A., Yokoyama, K., Muramatsu, M., Nishino T., and Obata, S., Gene cloning and overexpression of a geranylgeranyl diphosphate synthase of an extremely thermophilic bacterium, Thermus thermophilus. Biosci. Biotechnol. Biochem., 63, 261-270 (1999).
33. Koyama, T., Fujii, H., and Oguro, K., Enzymatic hydrolysis of polyprenyl pyrophosphate. Methods Enzymol., 110, 153-155 (1985)
34. Gibson, K. M., Lohr, J. L., Broock, R. L., Hoffmann, G., Nyhan, W. L., Sweetman, L., Brandt, I. K., Wappner, R. S., and Bader, P. I., Mevalonate kinase in lysates of cultured human fibroblasts and lymphoblasts: kinetic properties, assay conditions, carrier detection and measurement of residual activity in a patient with mevalonic aciduria. Enzyme, 41, 47-55 (1989).
35. Porter, J. W., Mevalonate kinase. Methods Enzymol., 110, 71-78 (1985).
36. Toth, M. J. and Huwyler, L., Molecular cloning and expression of the cDNAs encoding human and yeast mevalonate pyrophosphate decarboxylase. J. Biol. Chem., 271, 7895-7898 (1996).
37. Kaneda, K., Kuzuyama, T., Takagi, M., Hayakawa, Y., and Seto, H., An unusual isopentenyl diphosphate isomerase found in the mevalonate pathway gene cluster from Streptomyces sp. strain CL190. Proc. Natl. Acad. Sci. USA., 98, 932-937 (2001).
38. Dairi, T., Nakano, T., Aisaka, K., Katsumata, R., and Hasegawa, M., Cloning and nucleotide sequence of the gene responsible for chlorination of tetracycline. Biosci. Biotechnol. Biochem., 59, 1099-1106 (1995).
39. Pearson, W. R. and Lipman, D. J., Improved tools for biological sequence comparison. Proc. Natl. Acad. Sci. USA, 85, 2444-2448 (1988).
40. Altschul, S. F., Gish, W., Miller, W., Myers, E. W., and Lipman, D. J., Basic local alignment search tool. J. Mol. Biol., 215, 403-410 (1990).
41. Bibb, M. J., Findlay, P. R., and Johnson, M. W., The relatioship between base composition and codon usage in bacterial genes and its use in the simple and reliable identification of protein coding sequence. Gene, 30, 157-166 (1984).
42. Shin-ya, K., Imai, S., Furihata, K,. Hayakawa, Y., Kato, Y., VanDuyne, G. D., Clardy, J. and Seto, H., Isolation and structural elucidation of an antioxidative agent, naphterpin. J. Antibiot., 43, 444-447 (1990).