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Literature DB >> 21384874

A stereoselective vanadium-dependent chloroperoxidase in bacterial antibiotic biosynthesis.

Peter Bernhardt¹, Tatsufumi Okino, Jaclyn M Winter, Akimasa Miyanaga, Bradley S Moore.

Abstract

Halogenases catalyze reactions that introduce halogen atoms into electron-rich organic molecules. Vanadium-dependent haloperoxidases are generally considered to be promiscuous halogenating enzymes that have thus far been derived exclusively from eukaryotes, where their cellular function is often disputed. We now report the first biochemical characterization of a bacterial vanadium-dependent chloroperoxidase, NapH1 from Streptomyces sp. CNQ-525, which catalyzes a highly stereoselective chlorination-cyclization reaction in napyradiomycin antibiotic biosynthesis. This finding biochemically links a vanadium chloroperoxidase to microbial natural product biosynthesis.

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Year: 2011 PMID： 21384874 PMCID： PMC3065929 DOI： 10.1021/ja201088k

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

23 in total

1. Bromine is an endogenous component of a vanadium bromoperoxidase.

Authors: Martin C Feiters; Catherine Leblanc; Frithjof C Küpper; Wolfram Meyer-Klaucke; Gurvan Michel; Philippe Potin
Journal: J Am Chem Soc Date: 2005-11-09 Impact factor: 15.419

Review 2. Nature's inventory of halogenation catalysts: oxidative strategies predominate.

Authors: Frédéric H Vaillancourt; Ellen Yeh; David A Vosburg; Sylvie Garneau-Tsodikova; Christopher T Walsh
Journal: Chem Rev Date: 2006-08 Impact factor: 60.622

3. A80915, a new antibiotic complex produced by Streptomyces aculeolatus. Discovery, taxonomy, fermentation, isolation, characterization, and antibacterial evaluation.

Authors: D S Fukuda; J S Mynderse; P J Baker; D M Berry; L D Boeck; R C Yao; F P Mertz; W M Nakatsukasa; J Mabe; J Ott
Journal: J Antibiot (Tokyo) Date: 1990-06 Impact factor: 2.649

Review 4. Halogenation strategies in natural product biosynthesis.

Authors: Christopher S Neumann; Danica Galonić Fujimori; Christopher T Walsh
Journal: Chem Biol Date: 2008-02

5. Heterologous expression of the vanadium-containing chloroperoxidase from Curvularia inaequalis in Saccharomyces cerevisiae and site-directed mutagenesis of the active site residues His(496), Lys(353), Arg(360), and Arg(490).

Authors: W Hemrika; R Renirie; S Macedo-Ribeiro; A Messerschmidt; R Wever
Journal: J Biol Chem Date: 1999-08-20 Impact factor: 5.157

6. Antibiotic terpenoid chloro-dihydroquinones from a new marine actinomycete.

Authors: Irma E Soria-Mercado; Alejandra Prieto-Davo; Paul R Jensen; William Fenical
Journal: J Nat Prod Date: 2005-06 Impact factor: 4.050

7. Molecular basis for chloronium-mediated meroterpene cyclization: cloning, sequencing, and heterologous expression of the napyradiomycin biosynthetic gene cluster.

Authors: Jaclyn M Winter; Michelle C Moffitt; Emmanuel Zazopoulos; James B McAlpine; Pieter C Dorrestein; Bradley S Moore
Journal: J Biol Chem Date: 2007-03-28 Impact factor: 5.157

8. X-ray structure of a vanadium-containing enzyme: chloroperoxidase from the fungus Curvularia inaequalis.

Authors: A Messerschmidt; R Wever
Journal: Proc Natl Acad Sci U S A Date: 1996-01-09 Impact factor: 11.205

9. Purification, crystallisation and preliminary X-ray analysis of the vanadium-dependent haloperoxidase from Corallina officinalis.

Authors: C Rush; A Willetts; G Davies; Z Dauter; H Watson; J Littlechild
Journal: FEBS Lett Date: 1995-02-13 Impact factor: 4.124

10. Vanadium bromoperoxidase-catalyzed biosynthesis of halogenated marine natural products.

Authors: Jayme N Carter-Franklin; Alison Butler
Journal: J Am Chem Soc Date: 2004-11-24 Impact factor: 15.419

26 in total

1. Meroterpenoid natural products from Streptomyces bacteria - the evolution of chemoenzymatic syntheses.

Authors: Lauren A M Murray; Shaun M K McKinnie; Bradley S Moore; Jonathan H George
Journal: Nat Prod Rep Date: 2020-06-30 Impact factor: 13.423

2. The Vanadium Iodoperoxidase from the marine flavobacteriaceae species Zobellia galactanivorans reveals novel molecular and evolutionary features of halide specificity in the vanadium haloperoxidase enzyme family.

Authors: Jean-Baptiste Fournier; Etienne Rebuffet; Ludovic Delage; Romain Grijol; Laurence Meslet-Cladière; Justyna Rzonca; Philippe Potin; Gurvan Michel; Mirjam Czjzek; Catherine Leblanc
Journal: Appl Environ Microbiol Date: 2014-09-26 Impact factor: 4.792

A stereoselective vanadium-dependent chloroperoxidase in bacterial antibiotic biosynthesis.

1. Bromine is an endogenous component of a vanadium bromoperoxidase.

Review 2. Nature's inventory of halogenation catalysts: oxidative strategies predominate.

3. A80915, a new antibiotic complex produced by Streptomyces aculeolatus. Discovery, taxonomy, fermentation, isolation, characterization, and antibacterial evaluation.

Review 4. Halogenation strategies in natural product biosynthesis.

5. Heterologous expression of the vanadium-containing chloroperoxidase from Curvularia inaequalis in Saccharomyces cerevisiae and site-directed mutagenesis of the active site residues His(496), Lys(353), Arg(360), and Arg(490).

6. Antibiotic terpenoid chloro-dihydroquinones from a new marine actinomycete.

7. Molecular basis for chloronium-mediated meroterpene cyclization: cloning, sequencing, and heterologous expression of the napyradiomycin biosynthetic gene cluster.

8. X-ray structure of a vanadium-containing enzyme: chloroperoxidase from the fungus Curvularia inaequalis.

9. Purification, crystallisation and preliminary X-ray analysis of the vanadium-dependent haloperoxidase from Corallina officinalis.

10. Vanadium bromoperoxidase-catalyzed biosynthesis of halogenated marine natural products.

1. Meroterpenoid natural products from Streptomyces bacteria - the evolution of chemoenzymatic syntheses.

2. The Vanadium Iodoperoxidase from the marine flavobacteriaceae species Zobellia galactanivorans reveals novel molecular and evolutionary features of halide specificity in the vanadium haloperoxidase enzyme family.

Review 3. Oxidative Cyclization in Natural Product Biosynthesis.

4. A multitasking vanadium-dependent chloroperoxidase as an inspiration for the chemical synthesis of the merochlorins.

5. A unifying paradigm for naphthoquinone-based meroterpenoid (bio)synthesis.

6. Natural products as inspiration for the development of new synthetic methods.

Review 7. Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse.

8. Organohalide-Respiring Bacteria at the Heart of Anaerobic Metabolism in Arctic Wet Tundra Soils.

9. Enantioselective Synthesis of Azamerone.

10. Napyradiomycins CNQ525.510B and A80915C target the Hsp90 paralogue Grp94.