title: A membrane-bound prenyltransferase catalyzes the O-prenylation of 1,6-dihydroxyphenazine in the marine bacterium Streptomyces sp. CNQ-509.
abstract: 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 C-O 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.
authors.affiliation: Pharmazeutische Biologie, Pharmazeutisches Institut, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 8, 72076 Tübingen (Germany).
authors.forename: Philipp
authors.initials: P
authors.lastname: Zeyhle
authors.forename: Judith S
authors.initials: JS
authors.lastname: Bauer
authors.forename: Marco
authors.initials: M
authors.lastname: Steimle
authors.forename: Franziska
authors.initials: F
authors.lastname: Leipoldt
authors.forename: Manuela
authors.initials: M
authors.lastname: Rösch
authors.forename: Jörn
authors.initials: J
authors.lastname: Kalinowski
authors.forename: Harald
authors.initials: H
authors.lastname: Gross
authors.forename: Lutz
authors.initials: L
authors.lastname: Heide
mesh_terms: D001426:Bacterial Proteins / Q000378:metabolism*; D055162:Biocatalysis; D004122:Dimethylallyltranstransferase / Q000378:metabolism*; D007700:Kinetics; D005810:Multigene Family; D010619:Phenazines / Q000737:chemistry / Q000378:metabolism*; D054876:Prenylation; D013302:Streptomyces / Q000201:enzymology* / Q000235:genetics; D013379:Substrate Specificity
chemical_list: D001426:Bacterial Proteins; D010619:Phenazines; C037165:1-phenazinecarboxylic acid; D004122:Dimethylallyltranstransferase
keywords: Streptomyces; biosynthesis; enzyme catalysis; phenazine; prenyltransferase