The biosynthetic genes for prenylated phenazines are located at two different chromosomal loci of Streptomyces cinnamonensis DSM 1042

Microbial Biotechnology

Volumn 4, Issue 2, 2011, Pages 252-262

  Seeger, Kerstin ^a   Flinspach, Katrin ^a   Haug Schifferdecker, Elisa ^a   Kulik, Andreas ^a   Gust, Bertolt ^a   Fiedler, Hans Peter ^a   Heide, Lutz ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

5,10 DIHYDROPHENAZINE 1 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; DIMETHYLALLYL DIPHOSPHATE; ENDOPHENAZINE A; ENDOPHENAZINE B; FURANONAPHTHOQUINONE I; HYBRID PROTEIN; MEVALONIC ACID; PHENAZINE 1 CARBOXYLIC ACID; PHENAZINE DERIVATIVE; PYROPHOSPHATE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CHROMOSOME; BACTERIAL GENOME; BACTERIAL STRAIN; CATALYSIS; CATALYST; CONTROLLED STUDY; COSMID; ENZYME MECHANISM; ENZYME SUBSTRATE; ESCHERICHIA COLI; GENE LIBRARY; GENE LOCUS; GENE SEQUENCE; GENE SYNTHESIS; NONHUMAN; NUCLEOTIDE SEQUENCE; OPERON; PRENYLATION; PROTEIN EXPRESSION; PROTEIN PURIFICATION; PSEUDOMONAS; SEQUENCE HOMOLOGY; STREPTOMYCES; STREPTOMYCES CINNAMONEUS;

BACTERIAL PROTEINS; CHROMOSOMES, BACTERIAL; DIMETHYLALLYLTRANSTRANSFERASE; GENE EXPRESSION REGULATION, BACTERIAL; KINETICS; MOLECULAR SEQUENCE DATA; PHENAZINES; PRENYLATION; STREPTOMYCES;

ESCHERICHIA COLI; PSEUDOMONAS; STREPTOMYCES CINNAMONENSIS;

EID: 79951832427     PISSN: 17517907     EISSN: 17517915     Source Type: Journal    
DOI: 10.1111/j.1751-7915.2010.00234.x     Document Type: Article

References (31)

1. Ahuja, E.G., Janning, P., Mentel, M., Graebsch, A., Breinbauer, R., Hiller, W., etal. (2008) PhzA/B catalyzes the formation of the tricycle in phenazine biosynthesis. J Am Chem Soc 130: 17053-17061.
2. Binz, T.M., Wenzel, S.C., Schnell, H.J., Bechthold, A., and Müller, R. (2008) Heterologous expression and genetic engineering of the phenalinolactone biosynthetic gene cluster by using red/ET recombineering. Chembiochem 9: 447-454.
3. Bringmann, G., Haagen, Y., Gulder, T.A., Gulder, T., and Heide, L. (2007) Biosynthesis of the isoprenoid moieties of furanonaphthoquinone I and endophenazine A in Streptomyces cinnamonensis DSM 1042. J Org Chem 72: 4198-4204.
4. Dairi, T. (2005) Studies on biosynthetic genes and enzymes of isoprenoids produced by actinomycetes. J Antibiot 58: 227-243.
5. Dairi, T., Hamano, Y., Kuzuyama, T., Itoh, N., Furihata, K., and Seto, H. (2001) Eubacterial diterpene cyclase genes essential for production of the isoprenoid antibiotic terpentecin. J Bacteriol 183: 6085-6094.
6. Gebhardt, K., Schimana, J., Krastel, P., Dettner, K., Rheinheimer, J., Zeeck, A., and Fiedler, H.P. (2002) Endophenazines A-D, new phenazine antibiotics from the arthropod associated endosymbiont Streptomyces anulatus. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot 55: 794-800.
7. Gust, B., Chandra, G., Jakimowicz, D., Yuqing, T., Bruton, C.J., and Chater, K.F. (2004) Lambda red-mediated genetic manipulation of antibiotic-producing Streptomyces. Adv Appl Microbiol 54: 107-128.
8. Haagen, Y., Glück, K., Fay, K., Kammerer, B., Gust, B., and Heide, L. (2006) A gene cluster for prenylated naphthoquinone and prenylated phenazine biosynthesis in Streptomyces cinnamonensis DSM 1042. Chembiochem 7: 2016-2027.
9. Haagen, Y., Unsöld, I., Westrich, L., Gust, B., Richard, S.B., Noel, J.P., and Heide, L. (2007) A soluble, magnesium-independent prenyltransferase catalyzes reverse and regular C-prenylations and O-prenylations of aromatic substrates. FEBS Lett 581: 2889-2893.
10. Heide, L. (2009) Prenyl transfer to aromatic substrates: genetics and enzymology. Curr Opin Chem Biol 13: 171-179.
11. Jiang, J., He, X., and Cane, D.E. (2007) Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme. Nat Chem Biol 3: 711-715.
12. Kieser, T., Bibb, M.J., Buttner, M.J., Chater, K.F., and Hopwood, D.A. (2000) Practical Streptomyces Genetics. Norwich, UK: John Innes Foundation.
13. Kuzuyama, T., Noel, J.P., and Richard, S.B. (2005) Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products. Nature 435: 983-987.
14. Mavrodi, D.V., Ksenzenko, V.N., Bonsall, R.F., Cook, R.J., Boronin, A.M., and Thomashow, L.S. (1998) A seven-gene locus for synthesis of phenazine-1-carboxylic acid by Pseudomonas fluorescens 2-79. J Bacteriol 180: 2541-2548.
15. Mavrodi, D.V., Thomashow, L.S., and Blankenfeldt, W. (2008) Biosynthesis and regulation of phenazine compounds in Pseudomonas spp. In Pseudomonas. Rehm, B.H.A. (ed.). Weinheim, Germany: Wiley-VCH, pp. 331-351.
16. Mavrodi, D.V., Peever, T.L., Mavrodi, O.V., Parejko, J.A., Raaijmakers, J.M., Lemanceau, P., etal. (2010) Diversity and evolution of the phenazine biosynthesis pathway. Appl Environ Microbiol 76: 866-879.
17. Parsons, J.F., Calabrese, K., Eisenstein, E., and Ladner, J.E. (2004) Structure of the phenazine biosynthesis enzyme PhzG. Acta Crystallogr D Biol Crystallogr 60: 2110-2113.
18. Parsons, J.F., Greenhagen, B.T., Shi, K., Calabrese, K., Robinson, H., and Ladner, J.E. (2007) Structural and functional analysis of the pyocyanin biosynthetic protein PhzM from Pseudomonas aeruginosa. Biochemistry 46: 1821-1828.
19. Pojer, F., Wemakor, E., Kammerer, B., Chen, H., Walsh, C.T., Li, S.M., and Heide, L. (2003) CloQ, a prenyltransferase involved in clorobiocin biosynthesis. Proc Natl Acad Sci USA 100: 2316-2321.
20. Rose, T.M., Schultz, E.R., Henikoff, J.G., Pietrokovski, S., McCallum, C.M., and Henikoff, S. (1998) Consensus-degenerate hybrid oligonucleotide primers for amplification of distantly related sequences. Nucleic Acids Res 26: 1628-1635.
21. Rose, T., Henikoff, J., and Henikoff, S. (2003) codehop (COnsensus-DEgenerate Hybrid Oligonucleotide Primer) PCR primer design. Nucleic Acids Res 31: 3763-3766.
22. Saleh, O., Gust, B., Boll, B., Fiedler, H.P., and Heide, L. (2009a) Aromatic prenylation in phenazine biosynthesis: dihydrophenazine-1-carboxylate dimethylallyltransferase from Streptomyces anulatus. J Biol Chem 284: 14439-14447.
23. Saleh, O., Haagen, Y., Seeger, K., and Heide, L. (2009b) Prenyl transfer to aromatic substrates in the biosynthesis of aminocoumarins, meroterpenoids and phenazines: the ABBA prenyltransferase family. Phytochemistry 70: 1728-1738.
24. Sambrook, J., and Russell, D.W. (2001) Molecular Cloning. A Laboratory Manual. New York, USA: Cold Spring Harbor Laboratory Press.
25. Sedmera, P., Pospíšil, S., and Novák, J. (1991) New furanonaphthoquinone from Streptomyces cinnamonensis. J Nat Prod 54: 870-872.
26. Shin-ya, K., Furihata, K., Hayakawa, Y., and Seto, H. (1990) Biosynthetic studies of naphterpin, a terpenoid metabolite of Streptomyces. Tetrahedron Lett 31: 6025-6026.
27. Takahashi, S., Takagi, H., Toyoda, A., Uramoto, M., Nogawa, T., Ueki, M., etal. (2010) Biochemical characterization of a novel indole prenyltransferase from Streptomyces sp. SN-593. J Bacteriol 192: 2839-2851.
28. Tax, J., Sedmera, P., Vokoun, J., Urban, J., Karnetová, J., Stajner, K., etal. (1983) Phenazines from Streptomyces cinnamonensis. Collect Czech Chem Commun 48: 527-532.
29. Tello, M., Kuzuyama, T., Heide, L., Noel, J.P., and Richard, S.B. (2008) The ABBA family of aromatic prenyltransferases: broadening natural product diversity. Cell Mol Life Sci 65: 1459-1463.
30. Woodside, A.B., Huang, Z., and Poulter, C.D. (1993) Trisammonium geranyl diphosphate [diphosphoric acid, mono(3, 7-dimethyl-2, 6-octadienyl) ester (E)-, trisammonium salt]. Org Synth 66: 211-211.
31. Zhao, X.Q., Gust, B., and Heide, L. (2010) S-adenosylmethionine (SAM) and antibiotic biosynthesis: effect of external addition of SAM and of overexpression of SAM biosynthesis genes on novobiocin production in Streptomyces. Arch Microbiol 192: 289-297.