A membrane-bound prenyltransferase catalyzes the O-prenylation of 1,6-dihydroxyphenazine in the marine bacterium streptomyces sp. CNQ-509

ChemBioChem

Volumn 15, Issue 16, 2014, Pages 2385-2392

  Zeyhle, Philipp ^a   Bauer, Judith S ^a   Steimle, Marco ^a   Leipoldt, Franziska ^a   Rösch, Manuela ^a   Kalinowski, Jörn ^b   Gross, Harald ^a   Heide, Lutz ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b BIELEFELD UNIVERSITY   (Germany)

Author keywords

Biosynthesis; Enzyme catalysis; Phenazine; Prenyltransferase; Streptomyces

Indexed keywords

1,6 DIHYDROXYPHENAZINE; 1,6 DIHYDROXYPHENAZINE GERANYLTRANSFERASE; CARBON; DIMETHYLALLYLTRANSFERASE; GENOMIC DNA; OXYGEN; PHENAZINE DERIVATIVE; UBIQUINONE; UNCLASSIFIED DRUG; 1-PHENAZINECARBOXYLIC ACID; BACTERIAL PROTEIN;

ARTICLE; BACTERIAL GENOME; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CELLULAR DISTRIBUTION; CHEMICAL BOND; ENZYME ACTIVITY; ENZYME SPECIFICITY; GENE CLUSTER; HETERONUCLEAR MULTIPLE BOND CORRELATION; PRENYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES; BIOCATALYSIS; CHEMISTRY; ENZYMOLOGY; GENETICS; KINETICS; METABOLISM; MULTIGENE FAMILY;

BACTERIA (MICROORGANISMS); STREPTOMYCES; STREPTOMYCES SP.;

BACTERIAL PROTEINS; BIOCATALYSIS; DIMETHYLALLYLTRANSTRANSFERASE; KINETICS; MULTIGENE FAMILY; PHENAZINES; PRENYLATION; STREPTOMYCES; SUBSTRATE SPECIFICITY;

EID: 84919388943     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201402394     Document Type: Article

References (52)

1. a) W. Fenical, P. R. Jensen, Nat. Chem. Biol. 2006, 2, 666-673
2. b) C. C. Hughes, W. Fenical, Chem. Eur. J. 2010, 16, 12512-12525.
3. K. A. Gallagher, K. Rauscher, L. Pavan Ioca, P. R. Jensen, Appl. Environ. Microbiol. 2013, 79, 6894-6902.
4. a) C. Pathirana, PR. Jensen, W. Fenical, Tetrahedron Lett. 1992, 33, 7663-7666
5. b) J. Y Cho, H. C. Kwon, P. G. Williams, P. R. Jensen, W. Fenical, Org. Lett. 2006, 8, 2471-2474
6. c) I. E. Soria-Mercado, A. Prieto-Davo, P. R. Jensen, W. Fenical, J. Nat. Prod. 2005, 68, 904-910.
7. H. C. Kwon, A. P. D. M. Espindola, J.-S. Park, A. Prieto-Davó, M. Rose, P. R. Jensen, W. Fenical, J. Nat. Prod. 2010, 73, 2047-2052.
8. A. P. D. d. M. Espindola, Ph.D. Thesis, University of California, San Diego (USA), 2008.
9. Y Song, H. Huang, Y Chen, J. Ding, Y Zhang, A. Sun, W. Zhang, J. Ju, J. Nat. Prod. 2013, 76, 2263-2268.
10. H.-J. Abken, M. Tietze, J. Brodersen, S. Bäumer, U. Beifuss, U. Deppenmeier, J. Bacteriol. 1998, 180, 2027-2032.
11. a) O. Saleh, B. Gust, B. Boll, H.-P. Fiedler, L. Heide, J. Biol. Chem. 2009, 284, 14439-14447
12. b) K. Seeger, K. Flinspach, E. Haug-Schifferdecker, A. Kulik, B. Gust, H.-P. Fiedler, L. Heide, J. Microb. Biotechnol. 2011, 4, 252-262
13. c) P. Zeyhle, J. S. Bauer, J. Kalinowski, K. Shinya, H. Gross, L. Heide, PLoS One 2014, 9, e99122
14. d) D. Heine, K. Martin, C. Hertweck, J. Nat. Prod. 2014, 77, 1083-1087.
15. K. Blin, M. H. Medema, D. Kazempour, M. A. Fischbach, R. Breitling, E. Takano, T. Weber, Nucleic Acids Res. 2013, 41, W204-W212.
16. a) D. V. Mavrodi, V. N. Ksenzenko, R. F. Bonsall, R. J. Cook, A. M. Boronin, LS. Thomashow, J. Bacteriol. 1998, 180, 2541-2548
17. b) D.V. Mavrodi, R. F. Bonsall, S. M. Delaney, M.J. Soule, G. Phillips, LS. Thomashow, J. Bacteriol. 2001, 183, 6454-6465.
18. B. T. Greenhagen, K. Shi, H. Robinson, S. Gamage, A. K. Bera, J. E. Ladner, J. F. Parsons, Biochemistry 2008, 47, 5281-5289.
19. a) M. Tello, T. Kuzuyama, L. Heide, J. P. Noel, S. B. Richard, Cell. Mol. Life Sci. 2008, 65, 1459-1463
20. b) T. Bonitz, V. Alva, O. Saleh, A. N. Lupas, L. Heide, PLoS One 2011, 6, e27336.
21. M. McDonald, B. Wilkinson, C.W. Van't Land, U. Mocek, S. Lee, H.G. Floss, J. Am. Chem. Soc. 1999, 121, 5619-5624.
22. W. Blankenfeldt, A. P. Kuzin, T. Skarina, Y Korniyenko, L. Tong, P. Bayer, P. Janning, L. S. Thomashow, D. V. Mavrodi, Proc. Natl. Acad. Sci. USA 2004, 101, 16431-16436.
23. I.A. Mirza, B.J. Yachnin, S. Wang, S. Grosse, H. Bergeron, A. Imura, H. Iwaki, Y Hasegawa, P. C. K. Lau, A. M. Berghuis, J. Am. Chem. Soc. 2009, 131, 8848-8854.
24. M. Melzer, L. Heide, Biochim. Biophys. Acta Lipids Lipid Metab. 1994, 1212, 93-102.
25. A. Krogh, B. Larsson, G. von Heijne, E. L. L. Sonnhammer, J. Mol. Biol. 2001, 305, 567-580.
26. L. Heide, Curr. Opin. Chem. Biol. 2009, 13, 171-179.
27. L. Bräuer, W. Brandt, D. Schulze, S. Zakharova, L. Wessjohann, ChemBioChem 2008, 9, 982-992.
28. G. Zocher, O. Saleh, J. B. Heim, D. A. Herbst, L. Heide, T. Stehle, PLoS One 2012, 7, e48427.
29. K. Suvarna, D. Stevenson, R. Meganathan, M. E. S. Hudspeth, J. Bacteriol. 1998, 180, 2782-2787.
30. a) T Itoh, K. Tokunaga, Y Matsuda, I. Fujii, I. Abe, Y Ebizuka, T. Kushiro, Nat. Chem. 2010, 2, 858-864
31. b) J. Hu, H. Okawa, K. Yamamoto, K. Oyama, M. Mitomi, H. Anzai, J. Antibiot. 2011, 64, 221-227
32. c) T Itoh, K. Tokunaga, E. K. Radhakrishnan, I. Fujii, I. Abe, Y Ebizuka, T. Kushiro, ChemBioChem 2012, 13, 1132-1135
33. d) H.-C. Lo, R. Entwistle, C.-J. Guo, M. Ahuja, E. Szewczyk, J.-H. Hung, Y.-M. Chiang, B. R. Oakley, C. C. C. Wang, J. Am. Chem. Soc. 2012, 134, 4709-4720.
34. a) E. Stec, D. Pistorius, R. Müller, S.-M. Li, ChemBioChem 2011, 12, 1724-1730
35. b) T Kawasaki, T. Kuzuyama, K. Furihata, N. Itoh, H. Seto, T. Dairi, J. Antibiot. 2003, 56, 957-966
36. c) W. Kitagawa, T. Ozaki, T. Nishioka, Y Yasutake, M. Hata, M. Nishiyama, T. Kuzuyama, T. Tamura, ChemBioChem 2013, 14, 1085-1093.
37. T. Awakawa, N. Fujita, M. Hayakawa, Y Ohnishi, S. Horinouchi, ChemBioChem 2011, 12, 439-448.
38. Y Hayakawa, Y Yamazaki, M. Kurita, T. Kawasaki, M. Takagi, K. Shinya, J. Antibiot. 2010, 63, 379-380.
39. Y. Haagen, I. Unsöld, L. Westrich, B. Gust, S. B. Richard, J. P. Noel, L. Heide, FEBS Lett. 2007, 581, 2889-2893.
40. T. Kumano, T. Tomita, M. Nishiyama, T. Kuzuyama, J. Biol. Chem. 2010, 285, 39663-39671.
41. A. B. Woodside, Z. Huang, C. D. Poulter, Org. Synth. 1988, 66, 211.
42. F. Gross, N. Luniak, O. Perlova, N. Gaitatzis, H. Jenke-Kodama, K. Gerth, D. Gottschalk, E. Dittmann, R. Müller, Arch. Microbiol. 2006, 185, 28-38.
43. J. Sambrook, D. W. Russel, Molecular Cloning. A Laboratory Manual, 3edrd edCold Spring Harbor Laboratory Press, New York, 2001.
44. T. Kieser, M.J. Bibb, M.J. Buttner, K. F. Chater, D. A. Hopwood, Practical Streptomyces Genetics, John Innes Foundation, Norwich, 2000.
45. S. F. Altschul, T. L. Madden, A. A. Schäffer, J. Zhang, Z. Zhang, W. Miller, D. J. Lipman, Nucleic Acids Res. 1997, 25, 3389-3402.
46. K. Rutherford, J. Parkhill, J. Crook, T. Horsnell, P. Rice, M.-A. Rajandream, B. Barrell, Bioinformatics 2000, 16, 944-945.
47. E. Breitmaier, U. Hollstein, J. Org. Chem. 1976, 41, 2104-2108.
48. M. M. Bradford, Anal. Biochem. 1976, 72, 248-254.
49. A. Römer, Org. Magn. Reson. 1982, 19, 66-68.
50. a) P. A. Couperus, A. D. H. Clague, J. P. C. M. van Dongen, Org. Magn. Reson. 1976, 8, 426-431
51. b) H.-O. Kalinowski, S. Berger, S. Braun, Carbon-13 NMR Spectroscopy, Wiley, Chichester, 1988
52. c) M. Albericci, J. C. Braekman, D. Daloze, B. Tursch, J. P. Declercq, G. Germain, M. van Meerssche, Bull. Soc. Chim. Belg. 1978, 87, 487-492.