Novel tryptophan metabolism by a potential gene cluster that is widely distributed among actinomycetes

Journal of Biological Chemistry

Volumn 288, Issue 14, 2013, Pages 9946-9956

  Ozaki, Taro ^a   Nishiyama, Makoto ^a   Kuzuyama, Tomohisa ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMICAL CHARACTERIZATION; BIOSYNTHETIC GENE; FLAVIN-DEPENDENT MONOOXYGENASE; PRENYLTRANSFERASE; REACTION CATALYZED; STREPTOMYCES COELICOLOR A3(2); STREPTOMYCES LIVIDANS; STRUCTURAL DIVERSITY;

AMINO ACIDS; BACTERIA; BIOCHEMISTRY; BIOMOLECULES; BIOSYNTHESIS; CATALYSIS; ENZYMES; METABOLISM; METABOLITES; PHYSIOLOGY;

GENES;

5 DIMETHYLALLYL LEVO TRYPTOPHAN; 5 DIMETHYLALLYLINDOLE 3 ACETALDOXIME; 5 DIMETHYLALLYLINDOLE 3 ACETONITRILE; ACETALDOXIME; ACETONITRILE; DIMETHYLALLYLTRANSFERASE; TRYPTOPHAN; UNCLASSIFIED DRUG;

AMINO ACID METABOLISM; ARTICLE; BIOCHEMISTRY; BIOSYNTHESIS; CATALYSIS; ENZYME MECHANISM; GENE; GENE CLUSTER; GENE EXPRESSION; GENE FUNCTION; METABOLITE; NONHUMAN; PRENYLATION; PRIORITY JOURNAL; SCO7467 GENE; SCO7468 GENE; STREPTOMYCES COELICOLOR; STREPTOMYCES LIVIDANS;

ACTINOBACTERIA; CHROMATOGRAPHY, LIQUID; GENE EXPRESSION REGULATION, BACTERIAL; HEMITERPENES; INDOLES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, GENETIC; MULTIGENE FAMILY; PLASMIDS; RECOMBINANT PROTEINS; STREPTOMYCES; TANDEM MASS SPECTROMETRY; TERPENES; THIOURACIL; TRYPTOPHAN;

ACTINOBACTERIA (CLASS); STREPTOMYCES COELICOLOR; STREPTOMYCES LIVIDANS;

EID: 84875992701     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M112.436451     Document Type: Article

References (31)

1. Newman, D. J., and Cragg, G. M. (2007) Natural products as sources of new drugs over the last 25 years. J. Nat. Prod. 70, 461-477
2. Clardy, J., and Walsh, C. (2004) Lessons from natural molecules. Nature 432, 829-837
3. Ikeda, H., Ishikawa, J., Hanamoto, A., Shinose, M., Kikuchi, H., Shiba, T., Sakaki, Y., Hattori, M., and Omura, S. (2003) Complete genome sequence and comparative analysis of the industrial microorganism Streptomyces avermitilis. Nat. Biotechnol. 21, 526-531
4. Bentley, S. D., Chater, K. F., Cerdeño-Tárraga, A. M., Challis, G. L., Thomson, N. R., James, K. D., Harris, D. E., Quail, M. A., Kieser, H., Harper, D., Bateman, A., Brown, S., Chandra, G., Chen, C. W., Collins, M., Cronin, A., Fraser, A., Goble, A., Hidalgo, J., Hornsby, T., Howarth, S., Huang, C. H., Kieser, T., Larke, L., Murphy, L., Oliver, K., O'Neil, S., Rabbinowitsch, E., Rajandream, M. A., Rutherford, K., Rutter, S., Seeger, K., Saunders, D., Sharp, S., Squares, R., Squares, S., Taylor, K., Warren, T., Wietzorrek, A., Woodward, J., Barrell, B. G., Parkhill, J., and Hopwood, D. A. (2002) Complete genome sequence of the model actinomycete Streptomyces coelicolor A3(2). Nature 417, 141-147
5. Ohnishi, Y., Ishikawa, J., Hara, H., Suzuki, H., Ikenoya, M., Ikeda, H., Yamashita, A., Hattori, M., and Horinouchi, S. (2008) Genome sequence of the streptomycin-producing microorganism Streptomyces griseus IFO 13350. J. Bacteriol. 190, 4050-4060
6. Wilkinson, B., and Micklefield, J. (2007) Mining and engineering naturalproduct biosynthetic pathways. Nat. Chem. Biol. 3, 379-386
7. Bergmann, S., Schümann, J., Scherlach, K., Lange, C., Brakhage, A. A., and Hertweck, C. (2007) Genomics-driven discovery of PKS-NRPS hybrid metabolites from Aspergillus nidulans. Nat. Chem. Biol. 3, 213-217
8. Lautru, S., Deeth, R. J., Bailey, L. M., and Challis, G. L. (2005) Discovery of a new peptide natural product by Streptomyces coelicolor genome mining. Nat. Chem. Biol. 1, 265-269
9. Komatsu, M., Uchiyama, T., Omura, S., Cane, D. E., and Ikeda, H. (2010) Genome-minimized Streptomyces host for the heterologous expression of secondary metabolism. Proc. Natl. Acad. Sci. U.S.A. 107, 2646-2651
10. Takahashi, S., Takagi, H., Toyoda, A., Uramoto, M., Nogawa, T., Ueki, M., Sakaki, Y., and Osada, H. (2010) Biochemical characterization of a novel indole prenyltransferase from Streptomyces sp. SN-593. J. Bacteriol. 192, 2839-2851
11. Dairi, T., Aisaka, K., Katsumata, R., and Hasegawa, M. (1995) A self-defense gene homologous to tetracycline effluxing gene essential for antibiotic production in Streptomyces aureofaciens. Biosci. Biotechnol. Biochem. 59, 1835-1841
12. Isogai, S., Nishiyama, M., and Kuzuyama, T. (2012) Identification of 8- amino-2,5,7-trihydroxynaphthalene-1,4-dione, a novel intermediate in the biosynthesis of Streptomyces meroterpenoids. Bioorg. Med. Chem. Lett. 22, 5823-5826
13. Sambrook, J., and Russell, D. W. (2001) Molecular Cloning: A Laboratory Manual, 3rd Ed., Cold Spring Harbor Laboratory, Cold Spring Harbor, NY
14. Jez, J. M., Ferrer, J. L., Bowman, M. E., Dixon, R. A., and Noel, J. P. (2000) Dissection of malonyl-coenzyme A decarboxylation from polyketide formation in the reaction mechanism of a plant polyketide synthase. Biochemistry 39, 890-902
15. Kieser, T., Bibb, M. J., Buttner, M. J., Chater, K. F., and Hopwood, D. A. (eds) (2000) Practical Streptomyces Genetics, The John Innes Foundation, Norwich, CT
16. Ozaki, T., Mishima, S., Nishiyama, M., and Kuzuyama, T. (2009) NovQ is a prenyltransferase capable of catalyzing the addition of a dimethylallyl group to both phenylpropanoids and flavonoids. J. Antibiot. 62, 385-392
17. Ahmad, A. (1974) Syntheses of α-hydroxyamino acids from α-keto acids. Bull. Chem. Soc. Japan 47, 1819-1820
18. Kawase, Y., Yamagishi, T., Kutsuma, T., Ueda, K., Iwakuma, T., Nakata, T., and Yokomatsu, T. (2009) One-pot synthesis of alkoxyamine derivatives by reductive alkoxyamination with a 2-picoline-borane complex. Heterocycles 78, 463-470
19. Komatsu, M., Takano, H., Hiratsuka, T., Ishigaki, Y., Shimada, K., Beppu, T., and Ueda, K. (2006) Proteins encoded by the conservon of Streptomyces coelicolor A3(2) comprise a membrane-associated heterocomplex that resembles eukaryotic G protein-coupled regulatory system. Mol. Microbiol. 62, 1534-1546
20. Takano, H., Hashimoto, K., Yamamoto, Y., Beppu, T., and Ueda, K. (2011) Pleiotropic effect of a null mutation in the cvn1 conservon of Streptomyces coelicolor A3(2). Gene 477, 12-18
21. Komatsu, M., Kuwahara, Y., Hiroishi, A., Hosono, K., Beppu, T., and Ueda, K. (2003) Cloning of the conserved regulatory operon by its aerial mycelium- inducing activity in an amfR mutant of Streptomyces griseus. Gene 306, 79-89
22. Sibbesen, O., Koch, B., Halkier, B. A., and Møller, B. L. (1995) Cytochrome P-450TYR is a multifunctional heme-thiolate enzyme catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench. J. Biol. Chem. 270, 3506-3511
23. Yu, X., Liu, Y., Xie, X., Zheng, X. D., and Li, S. M. (2012) Biochemical characterization of indole prenyltransferases: filling the last gap of prenylation positions by a 5-dimethylallyltryptophan synthase from Aspergillus clavatus. J. Biol. Chem. 287, 1371-1380
24. Hull, A. K., Vij, R., and Celenza, J. L. (2000) Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis. Proc. Natl. Acad. Sci. U.S.A. 97, 2379-2384
25. Mikkelsen, M. D., Hansen, C. H., Wittstock, U., and Halkier, B. A. (2000) Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid. J. Biol. Chem. 275, 33712-33717
26. Lin, J., and Cashman, J. R. (1997)N-Oxygenation of phenethylamine to the trans-oxime by adult human liver flavin-containing monooxygenase and retroreduction of phenethylamine hydroxylamine by human liver microsomes. J. Pharmacol. Exp. Ther. 282, 1269-1279
27. Poulsen, L. L., Taylor, K., Williams, D. E., Masters, B. S., and Ziegler, D. M. (1986) Substrate specificity of the rabbit lung flavin-containing monooxygenase for amines: oxidation products of primary alkylamines. Mol. Pharmacol. 30, 680-685
28. Motohashi, K., Irie, K., Toda, T., Matsuo, Y., Kasai, H., Sue, M., Furihata, K., and Seto, H. (2008) Studies on terpenoids produced by actinomycetes: 5-dimethylallylindole-3-carboxylic acid and A80915G-8-acid produced by marine-derived Streptomyces sp. MS239. J. Antibiot. 61, 75- 80
29. Sánchez López, J. M., Martínez Insua, M., Pérez Baz, J., Fernández Puentes, J. L., and Cañedo Hernández, L. M. (2003) New cytotoxic indolic metabolites from a marine Streptomyces. J. Nat. Prod. 66, 863- 864
30. Sasaki, T., Igarashi, Y., Ogawa, M., and Furumai, T. (2002) Identification of 6-prenylindole as an antifungal metabolite of Streptomyces sp. TP-A0595 and synthesis and bioactivity of 6-substituted indoles. J. Antibiot. 55, 1009-1012
31. Ortiz-Castro, R., Díaz-Pérez, C., Martínez-Trujillo, M., del Río, R. E., Campos-García, J., and López-Bucio, J. (2011) Transkingdom signaling based on bacterial cyclodipeptides with auxin activity in plants. Proc. Natl. Acad. Sci. U.S.A. 108, 7253-7258