Literature DB >> 18721747

Cloning, expression, and biochemical characterization of Streptomyces rubellomurinus genes required for biosynthesis of antimalarial compound FR900098.

Andrew C Eliot1, Benjamin M Griffin, Paul M Thomas, Tyler W Johannes, Neil L Kelleher, Huimin Zhao, William W Metcalf.   

Abstract

The antibiotics n class="Chemical">fosmidomycin anclass="Chemical">pan>d FR900098 are members of a unique class of pan> class="Chemical">phosphonic acid natural products that inhibit the nonmevalonate pathway for n class="Chemical">isoprenoid biosynthesis. Both are potent antibacterial and antimalarial compounds, but despite their efficacy, little is known regarding their biosynthesis. Here we report the identification of the Streptomyces rubellomurinus genes required for the biosynthesis of FR900098. Expression of these genes in Streptomyces lividans results in production of FR900098, demonstrating their role in synthesis of the antibiotic. Analysis of the putative gene products suggests that FR900098 is synthesized by metabolic reactions analogous to portions of the tricarboxylic acid cycle. These data greatly expand our knowledge of phosphonate biosynthesis and enable efforts to overproduce this highly useful therapeutic agent.

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Year:  2008        PMID: 18721747      PMCID: PMC2603629          DOI: 10.1016/j.chembiol.2008.07.010

Source DB:  PubMed          Journal:  Chem Biol        ISSN: 1074-5521


  20 in total

1.  Basic local alignment search tool.

Authors:  S F Altschul; W Gish; W Miller; E W Myers; D J Lipman
Journal:  J Mol Biol       Date:  1990-10-05       Impact factor: 5.469

2.  Studies on the biosynthesis of bialaphos (SF-1293). 9. Biochemical mechanism of C-P bond formation in bialaphos: discovery of phosphoenolpyruvate phosphomutase which catalyzes the formation of phosphonopyruvate from phosphoenolpyruvate.

Authors:  T Hidaka; M Mori; S Imai; O Hara; K Nagaoka; H Seto
Journal:  J Antibiot (Tokyo)       Date:  1989-03       Impact factor: 2.649

3.  Purification and characterization of the Tetrahymena pyriformis P-C bond forming enzyme phosphoenolpyruvate phosphomutase.

Authors:  E D Bowman; M S McQueney; J D Scholten; D Dunaway-Mariano
Journal:  Biochemistry       Date:  1990-07-31       Impact factor: 3.162

4.  Genetically modified bacterial strains and novel bacterial artificial chromosome shuttle vectors for constructing environmental libraries and detecting heterologous natural products in multiple expression hosts.

Authors:  Asuncion Martinez; Steven J Kolvek; Choi Lai Tiong Yip; Joern Hopke; Kara A Brown; Ian A MacNeil; Marcia S Osburne
Journal:  Appl Environ Microbiol       Date:  2004-04       Impact factor: 4.792

5.  Studies on phosphonic acid antibiotics. IV. Synthesis and antibacterial activity of analogs of 3-(N-acetyl-N-hydroxyamino)-propylphosphonic acid (FR-900098).

Authors:  K Hemmi; H Takeno; M Hashimoto; T Kamiya
Journal:  Chem Pharm Bull (Tokyo)       Date:  1982-01       Impact factor: 1.645

6.  Studies on the biosynthesis of bialaphos (SF-1293). 8. Purification and characterization of 2-phosphinomethylmalic acid synthase from Streptomyces hygroscopicus SF-1293.

Authors:  K W Shimotohno; H Seto; N Otake; S Imai; T Murakami
Journal:  J Antibiot (Tokyo)       Date:  1988-08       Impact factor: 2.649

7.  Elucidation of the 2-aminoethylphosphonate biosynthetic pathway in Tetrahymena pyriformis.

Authors:  R J Barry; E Bowman; M McQueney; D Dunaway-Mariano
Journal:  Biochem Biophys Res Commun       Date:  1988-05-31       Impact factor: 3.575

8.  Phosphonate biosynthesis: isolation of the enzyme responsible for the formation of a carbon-phosphorus bond.

Authors:  H M Seidel; S Freeman; H Seto; J R Knowles
Journal:  Nature       Date:  1988-09-29       Impact factor: 49.962

9.  Studies on new phosphonic acid antibiotics. I. FR-900098, isolation and characterization.

Authors:  M Okuhara; Y Kuroda; T Goto; M Okamoto; H Terano; M Kohsaka; H Aoki; H Imanaka
Journal:  J Antibiot (Tokyo)       Date:  1980-01       Impact factor: 2.649

Review 10.  Malaria chemotherapeutics part I: History of antimalarial drug development, currently used therapeutics, and drugs in clinical development.

Authors:  Martin Schlitzer
Journal:  ChemMedChem       Date:  2007-07       Impact factor: 3.466

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  45 in total

1.  Characterization and structure of DhpI, a phosphonate O-methyltransferase involved in dehydrophos biosynthesis.

Authors:  Jin-Hee Lee; Brian Bae; Michael Kuemin; Benjamin T Circello; William W Metcalf; Satish K Nair; Wilfred A van der Donk
Journal:  Proc Natl Acad Sci U S A       Date:  2010-09-27       Impact factor: 11.205

2.  Characterization and application of the Fe(II) and α-ketoglutarate dependent hydroxylase FrbJ.

Authors:  Matthew A DeSieno; Wilfred A van der Donk; Huimin Zhao
Journal:  Chem Commun (Camb)       Date:  2011-08-10       Impact factor: 6.222

3.  Identification and heterologous expression of genes involved in anaerobic dissimilatory phosphite oxidation by Desulfotignum phosphitoxidans.

Authors:  Diliana Dancheva Simeonova; Marlena Marie Wilson; William W Metcalf; Bernhard Schink
Journal:  J Bacteriol       Date:  2010-07-09       Impact factor: 3.490

4.  Characterization of Two Late-Stage Enzymes Involved in Fosfomycin Biosynthesis in Pseudomonads.

Authors:  Philip Olivares; Emily C Ulrich; Jonathan R Chekan; Wilfred A van der Donk; Satish K Nair
Journal:  ACS Chem Biol       Date:  2016-12-27       Impact factor: 5.100

5.  Structural analysis of a phosphonate hydroxylase with an access tunnel at the back of the active site.

Authors:  Changqing Li; Muhammad Junaid; Eman Abdullah Almuqri; Shiguang Hao; Houjin Zhang
Journal:  Acta Crystallogr F Struct Biol Commun       Date:  2016-04-22       Impact factor: 1.056

6.  Purification and characterization of phosphonoglycans from Glycomyces sp. strain NRRL B-16210 and Stackebrandtia nassauensis NRRL B-16338.

Authors:  Xiaomin Yu; Neil P J Price; Bradley S Evans; William W Metcalf
Journal:  J Bacteriol       Date:  2014-02-28       Impact factor: 3.490

7.  Phylogenetic evidence for lateral gene transfer in the intestine of marine iguanas.

Authors:  David M Nelson; Isaac K O Cann; Eric Altermann; Roderick I Mackie
Journal:  PLoS One       Date:  2010-05-24       Impact factor: 3.240

8.  Diversity and abundance of phosphonate biosynthetic genes in nature.

Authors:  Xiaomin Yu; James R Doroghazi; Sarath C Janga; Jun Kai Zhang; Benjamin Circello; Benjamin M Griffin; David P Labeda; William W Metcalf
Journal:  Proc Natl Acad Sci U S A       Date:  2013-12-02       Impact factor: 11.205

9.  Discovery of the antibiotic phosacetamycin via a new mass spectrometry-based method for phosphonic acid detection.

Authors:  Bradley S Evans; Changming Zhao; Jiangtao Gao; Courtney M Evans; Kou-San Ju; James R Doroghazi; Wilfred A van der Donk; Neil L Kelleher; William W Metcalf
Journal:  ACS Chem Biol       Date:  2013-03-13       Impact factor: 5.100

10.  Discovery of phosphonic acid natural products by mining the genomes of 10,000 actinomycetes.

Authors:  Kou-San Ju; Jiangtao Gao; James R Doroghazi; Kwo-Kwang A Wang; Christopher J Thibodeaux; Steven Li; Emily Metzger; John Fudala; Joleen Su; Jun Kai Zhang; Jaeheon Lee; Joel P Cioni; Bradley S Evans; Ryuichi Hirota; David P Labeda; Wilfred A van der Donk; William W Metcalf
Journal:  Proc Natl Acad Sci U S A       Date:  2015-08-31       Impact factor: 11.205

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