Genome-Based Discovery of a Novel Membrane-Bound 1,6-Dihydroxyphenazine Prenyltransferase from a Marine Actinomycete

作者: Philipp Zeyhle , Judith S. Bauer , Jörn Kalinowski , Kazuo Shin-ya , Harald Gross

DOI: 10.1371/JOURNAL.PONE.0099122

关键词:

摘要: Recently, novel prenylated derivatives of 1,6-dihydroxyphenazine have been isolated from the marine sponge-associated Streptomyces sp. SpC080624SC-11. Genome sequencing this strain now revealed a gene cluster containing all genes necessary for synthesis phenazine and isoprenoid moieties. Unexpectedly, however, did not contain with similarity to previously investigated prenyltransferases, but instead modest membrane-bound prenyltransferases ubiquinone menaquinone biosynthesis. Expression in E. coli isolation membrane fraction proved that encoded enzyme, Mpz10, catalyzes two successive prenylations 1,6-dihydroxyphenazine. Mpz10 is first example enzyme catalyzing prenylation substrate, one few examples enzymes involved aromatic secondary metabolites microorganisms.

参考文章(52)
K. Suvarna, D. Stevenson, R. Meganathan, M. E. S. Hudspeth, Menaquinone (vitamin K2) biosynthesis: localization and characterization of the menA gene from Escherichia coli. Journal of Bacteriology. ,vol. 180, pp. 2782- 2787 ,(1998) , 10.1128/JB.180.10.2782-2787.1998
Kerstin Seeger, Katrin Flinspach, Elisa Haug-Schifferdecker, Andreas Kulik, Bertolt Gust, Hans-Peter Fiedler, Lutz Heide, The biosynthetic genes for prenylated phenazines are located at two different chromosomal loci of Streptomyces cinnamonensis DSM 1042. Microbial Biotechnology. ,vol. 4, pp. 252- 262 ,(2011) , 10.1111/J.1751-7915.2010.00234.X
Dmitri V. Mavrodi, James A. Parejko, Olga V. Mavrodi, Youn-Sig Kwak, David M. Weller, Wulf Blankenfeldt, Linda S. Thomashow, Recent insights into the diversity, frequency and ecological roles of phenazines in fluorescent Pseudomonas spp. Environmental Microbiology. ,vol. 15, pp. 675- 686 ,(2013) , 10.1111/J.1462-2920.2012.02846.X
Shams Tabrez Khan, Miho Izumikawa, Keiichiro Motohashi, Akira Mukai, Motoki Takagi, Kazuo Shin-Ya, Distribution of the 3-hydroxyl-3-methylglutaryl coenzyme A reductase gene and isoprenoid production in marine-derived Actinobacteria Fems Microbiology Letters. ,vol. 304, pp. 89- 96 ,(2010) , 10.1111/J.1574-6968.2009.01886.X
Tobias Kieser, Mervyn J Bibb, Mark J Buttner, Keith F Chater, David A Hopwood, Practical streptomyces genetics John Innes Foundation. ,(2000)
Gerhard Bringmann, Yvonne Haagen, Tobias A. M. Gulder, Tanja Gulder, Lutz Heide, Biosynthesis of the isoprenoid moieties of furanonaphthoquinone I and endophenazine A in Streptomyces cinnamonensis DSM 1042. Journal of Organic Chemistry. ,vol. 72, pp. 4198- 4204 ,(2007) , 10.1021/JO0703404
Eberhard. Breitmaier, Ulrich. Hollstein, Carbon-13 nuclear magnetic resonance chemical shifts of substituted phenazines Journal of Organic Chemistry. ,vol. 41, pp. 2104- 2108 ,(1976) , 10.1021/JO00874A008
Imene Zendah, Naheed Riaz, Hamdi Nasr, Holm Frauendorf, Anja Schüffler, Aly Raies, Hartmut Laatsch, Chromophenazines from the terrestrial Streptomyces sp. Ank 315. Journal of Natural Products. ,vol. 75, pp. 2- 8 ,(2012) , 10.1021/NP100818D
Ekta G. Ahuja, Petra Janning, Matthias Mentel, Almut Graebsch, Rolf Breinbauer, Wolf Hiller, Burkhard Costisella, Linda S. Thomashow, Dmitri V. Mavrodi, Wulf Blankenfeldt, PhzA/B Catalyzes the Formation of the Tricycle in Phenazine Biosynthesis Journal of the American Chemical Society. ,vol. 130, pp. 17053- 17061 ,(2008) , 10.1021/JA806325K
TAKASHI KAWASAKI, TOMOHISA KUZUYAMA, KAZUO FURIHATA, NOBUYA ITOH, HARUO SETO, TOHRU DAIRI, A relationship between the mevalonate pathway and isoprenoid production in actinomycetes. The Journal of Antibiotics. ,vol. 56, pp. 957- 966 ,(2003) , 10.7164/ANTIBIOTICS.56.957