A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine Bacterium Streptomyces sp CNQ-509

Zeyhle P, Bauer JS, Steimle M, Leipoldt F, Roesch M, Kalinowski J, Gross H, Heide L (2014)
ChemBioChem 15(16): 2385-2392.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Zeyhle, Philipp; Bauer, Judith S.; Steimle, Marco; Leipoldt, Franziska; Roesch, Manuela; Kalinowski, JörnUniBi; Gross, Harald; Heide, Lutz
Abstract / Bemerkung
Streptomyces sp. CNQ-509 produces the rare O-prenylated phenazines marinophenazines A and B. To identify the enzyme catalyzing the O-prenyl transfer in marinophenazine biosynthesis, we sequenced the genome of S. sp. CNQ-509. This led to the identification of two genomic loci harboring putative phenazine biosynthesis genes. The first locus contains orthologues for all seven genes involved in phenazine-1-carboxylic acid biosynthesis in pseudomonads. The second locus contains two known phenazine biosynthesis genes and a putative prenyltransferase gene termed cnqPT1. cnqPT1 codes for a membrane protein with sequence similarity to the prenyltransferase UbiA of ubiquinone biosynthesis. The enzyme CnqPT1 was identified as a 1,6-dihydroxyphenazine geranyltransferase, which catalyzes the CO bond formation between C-1 of the geranyl moiety and O-6 of the phenazine scaffold. CnqPT1 is the first example of a prenyltransferase catalyzing O-prenyl transfer to a phenazine.
Stichworte
Streptomyces; prenyltransferase; phenazine; biosynthesis; enzyme catalysis
Erscheinungsjahr
2014
Zeitschriftentitel
ChemBioChem
Band
15
Ausgabe
16
Seite(n)
2385-2392
ISSN
1439-4227
Page URI
https://pub.uni-bielefeld.de/record/2707667

Zitieren

Zeyhle P, Bauer JS, Steimle M, et al. A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine Bacterium Streptomyces sp CNQ-509. ChemBioChem. 2014;15(16):2385-2392.
Zeyhle, P., Bauer, J. S., Steimle, M., Leipoldt, F., Roesch, M., Kalinowski, J., Gross, H., et al. (2014). A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine Bacterium Streptomyces sp CNQ-509. ChemBioChem, 15(16), 2385-2392. doi:10.1002/cbic.201402394
Zeyhle, Philipp, Bauer, Judith S., Steimle, Marco, Leipoldt, Franziska, Roesch, Manuela, Kalinowski, Jörn, Gross, Harald, and Heide, Lutz. 2014. “A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine Bacterium Streptomyces sp CNQ-509”. ChemBioChem 15 (16): 2385-2392.
Zeyhle, P., Bauer, J. S., Steimle, M., Leipoldt, F., Roesch, M., Kalinowski, J., Gross, H., and Heide, L. (2014). A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine Bacterium Streptomyces sp CNQ-509. ChemBioChem 15, 2385-2392.
Zeyhle, P., et al., 2014. A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine Bacterium Streptomyces sp CNQ-509. ChemBioChem, 15(16), p 2385-2392.
P. Zeyhle, et al., “A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine Bacterium Streptomyces sp CNQ-509”, ChemBioChem, vol. 15, 2014, pp. 2385-2392.
Zeyhle, P., Bauer, J.S., Steimle, M., Leipoldt, F., Roesch, M., Kalinowski, J., Gross, H., Heide, L.: A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine Bacterium Streptomyces sp CNQ-509. ChemBioChem. 15, 2385-2392 (2014).
Zeyhle, Philipp, Bauer, Judith S., Steimle, Marco, Leipoldt, Franziska, Roesch, Manuela, Kalinowski, Jörn, Gross, Harald, and Heide, Lutz. “A Membrane-Bound Prenyltransferase Catalyzes the O-Prenylation of 1,6-Dihydroxyphenazine in the Marine Bacterium Streptomyces sp CNQ-509”. ChemBioChem 15.16 (2014): 2385-2392.

9 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Draft Genome Sequence of the Novonestmycin-Producing Strain Streptomyces sp. Z26, Isolated from Potato Rhizosphere in Morocco.
Buchmann A, Cano-Prieto C, Nafis A, Barakate M, Baz M, Hassani L, Ortlieb N, Niedermeyer THJ, Gross H., Microbiol Resour Announc 8(1), 2019
PMID: 30637404
Draft Genome Sequence of the Xanthocidin-Producing Strain Streptomyces sp. AcE210, Isolated from a Root Nodule of Alnus glutinosa (L.).
Ortlieb N, Keilhofer N, Schrey SD, Gross H, Niedermeyer THJ., Microbiol Resour Announc 7(14), 2018
PMID: 30533708
Discovery and Characterization of a New Family of Diterpene Cyclases in Bacteria and Fungi.
Yang YL, Zhang S, Ma K, Xu Y, Tao Q, Chen Y, Chen J, Guo S, Ren J, Wang W, Tao Y, Yin WB, Liu H., Angew Chem Int Ed Engl 56(17), 2017
PMID: 28371074
Marine natural products.
Blunt JW, Copp BR, Keyzers RA, Munro MH, Prinsep MR., Nat Prod Rep 33(3), 2016
PMID: 26837534
Prenyltransferases as key enzymes in primary and secondary metabolism.
Winkelblech J, Fan A, Li SM., Appl Microbiol Biotechnol 99(18), 2015
PMID: 26216239

60 References

Daten bereitgestellt von Europe PubMed Central.


AUTHOR UNKNOWN, 0
Developing a new resource for drug discovery: marine actinomycete bacteria.
Fenical W, Jensen PR., Nat. Chem. Biol. 2(12), 2006
PMID: 17108984
Antibacterials from the sea.
Hughes CC, Fenical W., Chemistry 16(42), 2010
PMID: 20845412
Phylogenetic and chemical diversity of a hybrid-isoprenoid-producing streptomycete lineage.
Gallagher KA, Rauscher K, Pavan Ioca L, Jensen PR., Appl. Environ. Microbiol. 79(22), 2013
PMID: 23995934

AUTHOR UNKNOWN, 0

Pathirana, Tetrahedron Lett. 33(), 1992
Antibiotic terpenoid chloro-dihydroquinones from a new marine actinomycete.
Soria-Mercado IE, Prieto-Davo A, Jensen PR, Fenical W., J. Nat. Prod. 68(6), 2005
PMID: 15974616
Nitropyrrolins A-E, cytotoxic farnesyl-α-nitropyrroles from a marine-derived bacterium within the actinomycete family Streptomycetaceae.
Kwon HC, Espindola AP, Park JS, Prieto-Davo A, Rose M, Jensen PR, Fenical W., J. Nat. Prod. 73(12), 2010
PMID: 21090803

AUTHOR UNKNOWN, 0
Cytotoxic and antibacterial marfuraquinocins from the deep South China Sea-derived Streptomyces niveus SCSIO 3406.
Song Y, Huang H, Chen Y, Ding J, Zhang Y, Sun A, Zhang W, Ju J., J. Nat. Prod. 76(12), 2013
PMID: 24251399
Isolation and characterization of methanophenazine and function of phenazines in membrane-bound electron transport of Methanosarcina mazei Go1.
Abken HJ, Tietze M, Brodersen J, Baumer S, Beifuss U, Deppenmeier U., J. Bacteriol. 180(8), 1998
PMID: 9555882

AUTHOR UNKNOWN, 0
The biosynthetic genes for prenylated phenazines are located at two different chromosomal loci of Streptomyces cinnamonensis DSM 1042.
Seeger K, Flinspach K, Haug-Schifferdecker E, Kulik A, Gust B, Fiedler HP, Heide L., Microb Biotechnol 4(2), 2010
PMID: 21342470
Genome-based discovery of a novel membrane-bound 1,6-dihydroxyphenazine prenyltransferase from a marine actinomycete.
Zeyhle P, Bauer JS, Kalinowski J, Shin-ya K, Gross H, Heide L., PLoS ONE 9(6), 2014
PMID: 24892559
Genomics-guided discovery of endophenazines from Kitasatospora sp. HKI 714.
Heine D, Martin K, Hertweck C., J. Nat. Prod. 77(4), 2014
PMID: 24617951
antiSMASH 2.0--a versatile platform for genome mining of secondary metabolite producers.
Blin K, Medema MH, Kazempour D, Fischbach MA, Breitling R, Takano E, Weber T., Nucleic Acids Res. 41(Web Server issue), 2013
PMID: 23737449

AUTHOR UNKNOWN, 0
A seven-gene locus for synthesis of phenazine-1-carboxylic acid by Pseudomonas fluorescens 2-79.
Mavrodi DV, Ksenzenko VN, Bonsall RF, Cook RJ, Boronin AM, Thomashow LS., J. Bacteriol. 180(9), 1998
PMID: 9573209
Functional analysis of genes for biosynthesis of pyocyanin and phenazine-1-carboxamide from Pseudomonas aeruginosa PAO1.
Mavrodi DV, Bonsall RF, Delaney SM, Soule MJ, Phillips G, Thomashow LS., J. Bacteriol. 183(21), 2001
PMID: 11591691
Crystal structure of the pyocyanin biosynthetic protein PhzS.
Greenhagen BT, Shi K, Robinson H, Gamage S, Bera AK, Ladner JE, Parsons JF., Biochemistry 47(19), 2008
PMID: 18416536

AUTHOR UNKNOWN, 0
The ABBA family of aromatic prenyltransferases: broadening natural product diversity.
Tello M, Kuzuyama T, Heide L, Noel JP, Richard SB., Cell. Mol. Life Sci. 65(10), 2008
PMID: 18322648
Evolutionary relationships of microbial aromatic prenyltransferases.
Bonitz T, Alva V, Saleh O, Lupas AN, Heide L., PLoS ONE 6(11), 2011
PMID: 22140437

McDonald, J. Am. Chem. Soc. 121(), 1999
Structure and function of the phenazine biosynthetic protein PhzF from Pseudomonas fluorescens.
Blankenfeldt W, Kuzin AP, Skarina T, Korniyenko Y, Tong L, Bayer P, Janning P, Thomashow LS, Mavrodi DV., Proc. Natl. Acad. Sci. U.S.A. 101(47), 2004
PMID: 15545603
Crystal structures of cyclohexanone monooxygenase reveal complex domain movements and a sliding cofactor.
Mirza IA, Yachnin BJ, Wang S, Grosse S, Bergeron H, Imura A, Iwaki H, Hasegawa Y, Lau PC, Berghuis AM., J. Am. Chem. Soc. 131(25), 2009
PMID: 19385644
Predicting transmembrane protein topology with a hidden Markov model: application to complete genomes.
Krogh A, Larsson B, von Heijne G, Sonnhammer EL., J. Mol. Biol. 305(3), 2001
PMID: 11152613
Prenyl transfer to aromatic substrates: genetics and enzymology.
Heide L., Curr Opin Chem Biol 13(2), 2009
PMID: 19299193
A structural model of the membrane-bound aromatic prenyltransferase UbiA from E. coli.
Brauer L, Brandt W, Schulze D, Zakharova S, Wessjohann L., Chembiochem 9(6), 2008
PMID: 18338424
Structure-based engineering increased the catalytic turnover rate of a novel phenazine prenyltransferase.
Zocher G, Saleh O, Heim JB, Herbst DA, Heide L, Stehle T., PLoS ONE 7(10), 2012
PMID: 23119011
Menaquinone (vitamin K2) biosynthesis: localization and characterization of the menA gene from Escherichia coli.
Suvarna K, Stevenson D, Meganathan R, Hudspeth ME., J. Bacteriol. 180(10), 1998
PMID: 9573170

AUTHOR UNKNOWN, 0
Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases.
Itoh T, Tokunaga K, Matsuda Y, Fujii I, Abe I, Ebizuka Y, Kushiro T., Nat Chem 2(10), 2010
PMID: 20861902
Identification of a key prenyltransferase involved in biosynthesis of the most abundant fungal meroterpenoids derived from 3,5-dimethylorsellinic acid.
Itoh T, Tokunaga K, Radhakrishnan EK, Fujii I, Abe I, Ebizuka Y, Kushiro T., Chembiochem 13(8), 2012
PMID: 22549923
Two separate gene clusters encode the biosynthetic pathway for the meroterpenoids austinol and dehydroaustinol in Aspergillus nidulans.
Lo HC, Entwistle R, Guo CJ, Ahuja M, Szewczyk E, Hung JH, Chiang YM, Oakley BR, Wang CC., J. Am. Chem. Soc. 134(10), 2012
PMID: 22329759

AUTHOR UNKNOWN, 0
A relationship between the mevalonate pathway and isoprenoid production in actinomycetes.
Kawasaki T, Kuzuyama T, Furihata K, Itoh N, Seto H, Dairi T., J. Antibiot. 56(11), 2003
PMID: 14763562
Cloning and heterologous expression of the aurachin RE biosynthesis gene cluster afford a new cytochrome P450 for quinoline N-hydroxylation.
Kitagawa W, Ozaki T, Nishioka T, Yasutake Y, Hata M, Nishiyama M, Kuzuyama T, Tamura T., Chembiochem 14(9), 2013
PMID: 23677853
Characterization of the biosynthesis gene cluster for alkyl-O-dihydrogeranyl-methoxyhydroquinones in Actinoplanes missouriensis.
Awakawa T, Fujita N, Hayakawa M, Ohnishi Y, Horinouchi S., Chembiochem 12(3), 2011
PMID: 21264995
Flaviogeranin, a new neuroprotective compound from Streptomyces sp.
Hayakawa Y, Yamazaki Y, Kurita M, Kawasaki T, Takagi M, Shin-Ya K., J. Antibiot. 63(7), 2010
PMID: 20485338
A soluble, magnesium-independent prenyltransferase catalyzes reverse and regular C-prenylations and O-prenylations of aromatic substrates.
Haagen Y, Unsold I, Westrich L, Gust B, Richard SB, Noel JP, Heide L., FEBS Lett. 581(16), 2007
PMID: 17543953

Woodside, Org. Synth. 66(), 1988
Bacterial type III polyketide synthases: phylogenetic analysis and potential for the production of novel secondary metabolites by heterologous expression in pseudomonads.
Gross F, Luniak N, Perlova O, Gaitatzis N, Jenke-Kodama H, Gerth K, Gottschalk D, Dittmann E, Muller R., Arch. Microbiol. 185(1), 2006
PMID: 16395556

Sambrook, 2001

Kieser, 2000
Gapped BLAST and PSI-BLAST: a new generation of protein database search programs.
Altschul SF, Madden TL, Schaffer AA, Zhang J, Zhang Z, Miller W, Lipman DJ., Nucleic Acids Res. 25(17), 1997
PMID: 9254694
Artemis: sequence visualization and annotation.
Rutherford K, Parkhill J, Crook J, Horsnell T, Rice P, Rajandream MA, Barrell B., Bioinformatics 16(10), 2000
PMID: 11120685

Breitmaier, J. Org. Chem. 41(), 1976

Römer, Org. Magn. Reson. 19(), 1982

AUTHOR UNKNOWN, 0

Couperus, Org. Magn. Reson. 8(), 1976

Kalinowski, 1988

Albericci, Bull. Soc. Chim. Belg. 87(), 1978
Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 25224759
PubMed | Europe PMC

Suchen in

Google Scholar