Literature DB >> 17881282

What's new in enzymatic halogenations.

Danica Galonić Fujimori1, Christopher T Walsh.   

Abstract

The halogenation of thousands of natural products occurs during biosynthesis and often confers important functional properties. While haloperoxidases had been the default paradigm for enzymatic incorporation of halogens, via X+ equivalents into organic scaffolds, a combination of microbial genome sequencing, enzymatic studies and structural biology have provided deep new insights into enzymatic transfer of halide equivalents in three oxidation states. These are (1) the halide ions (X-) abundant in nature, (2) halogen atoms (X*), and (3) the X+ equivalents. The mechanism of halogen incorporation is tailored to the electronic demands of specific substrates and involves enzymes with distinct redox coenzyme requirements.

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Year:  2007        PMID: 17881282      PMCID: PMC2151916          DOI: 10.1016/j.cbpa.2007.08.002

Source DB:  PubMed          Journal:  Curr Opin Chem Biol        ISSN: 1367-5931            Impact factor:   8.822


  58 in total

1.  Barbamide, a chlorinated metabolite with molluscicidal activity from the Caribbean cyanobacterium Lyngbya majuscula.

Authors:  J Orjala; W H Gerwick
Journal:  J Nat Prod       Date:  1996-04       Impact factor: 4.050

Review 2.  Glycopeptide and lipoglycopeptide antibiotics.

Authors:  Dan Kahne; Catherine Leimkuhler; Wei Lu; Christopher Walsh
Journal:  Chem Rev       Date:  2005-02       Impact factor: 60.622

3.  A regioselective tryptophan 5-halogenase is involved in pyrroindomycin biosynthesis in Streptomyces rugosporus LL-42D005.

Authors:  Susanne Zehner; Alexander Kotzsch; Bojan Bister; Roderich D Süssmuth; Carmen Méndez; José A Salas; Karl-Heinz van Pée
Journal:  Chem Biol       Date:  2005-04

Review 4.  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

5.  Cloning and expression of genes required for coronamic Acid (2-ethyl-1-aminocyclopropane 1-carboxylic Acid), an intermediate in the biosynthesis of the phytotoxin coronatine.

Authors:  M Ullrich; A C Guenzi; R E Mitchell; C L Bender
Journal:  Appl Environ Microbiol       Date:  1994-08       Impact factor: 4.792

6.  Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens Pf-5.

Authors:  B Nowak-Thompson; N Chaney; J S Wing; S J Gould; J E Loper
Journal:  J Bacteriol       Date:  1999-04       Impact factor: 3.490

7.  The barbamide biosynthetic gene cluster: a novel marine cyanobacterial system of mixed polyketide synthase (PKS)-non-ribosomal peptide synthetase (NRPS) origin involving an unusual trichloroleucyl starter unit.

Authors:  Zunxue Chang; Patricia Flatt; William H Gerwick; Viet-Anh Nguyen; Christine L Willis; David H Sherman
Journal:  Gene       Date:  2002-08-21       Impact factor: 3.688

8.  Sequencing and analysis of genes involved in the biosynthesis of a vancomycin group antibiotic.

Authors:  A M van Wageningen; P N Kirkpatrick; D H Williams; B R Harris; J K Kershaw; N J Lennard; M Jones; S J Jones; P J Solenberg
Journal:  Chem Biol       Date:  1998-03

Review 9.  Microbial biosynthesis of halometabolites.

Authors:  K H van Pée
Journal:  Arch Microbiol       Date:  2001-04       Impact factor: 2.552

10.  Purification and Partial Characterization of Tryptophan 7-Halogenase (PrnA) from Pseudomonas fluorescens This work was supported by the Deutsche Forschungsgemeinschaft (DFG) through the Graduiertenkolleg "Struktur-Eigenschafts-Beziehungen bei Heterocyclen", the Environment and Climate Research and Technology Development Programme of the European Union, the Sächsische Staatsministerium für Umwelt und Landesentwicklung, the Max-Buchner-Stiftung, and the Fonds der Chemischen Industrie. Samples of P. fluorescens BL915DeltaORF1-4 with pPEH14(prnA) and pPEH14(prnC) were obtained from Dr. J. M. Ligon, Novartis Agribusiness Biotechnology Research, Inc., Research Triangle, NC (USA) and NADH oxidase (from Thermus thermiphilus) from Prof. Helmut Erdmann, Fachhochschule Flensburg (Germany).

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-07-03       Impact factor: 15.336

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  16 in total

1.  Conformational switch triggered by alpha-ketoglutarate in a halogenase of curacin A biosynthesis.

Authors:  Dheeraj Khare; Bo Wang; Liangcai Gu; Jamie Razelun; David H Sherman; William H Gerwick; Kristina Håkansson; Janet L Smith
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-26       Impact factor: 11.205

2.  Recognition of (2S)-aminomalonyl-acyl carrier protein (ACP) and (2R)-hydroxymalonyl-ACP by acyltransferases in zwittermicin A biosynthesis.

Authors:  Yolande A Chan; Michael G Thomas
Journal:  Biochemistry       Date:  2010-05-04       Impact factor: 3.162

3.  Stereochemical studies of the type II isopentenyl diphosphate-dimethylallyl diphosphate isomerase implicate the FMN coenzyme in substrate protonation.

Authors:  Jordi Calveras; Christopher J Thibodeaux; Steven O Mansoorabadi; Hung-wen Liu
Journal:  Chembiochem       Date:  2011-12-01       Impact factor: 3.164

Review 4.  Marine-derived metabolites of S-adenosylmethionine as templates for new anti-infectives.

Authors:  Janice R Sufrin; Steven Finckbeiner; Colin M Oliver
Journal:  Mar Drugs       Date:  2009-08-26       Impact factor: 5.118

Review 5.  Mechanistic considerations of halogenating enzymes.

Authors:  Alison Butler; Moriah Sandy
Journal:  Nature       Date:  2009-08-13       Impact factor: 49.962

6.  Enzymatic synthesis of bromo- and chlorocarbazoles and elucidation of their structures by molecular modeling.

Authors:  John Mumbo; Dieter Lenoir; Bernhard Henkelmann; Karl-Werner Schramm
Journal:  Environ Sci Pollut Res Int       Date:  2013-06-12       Impact factor: 4.223

Review 7.  Environmental Control of Vanadium Haloperoxidases and Halocarbon Emissions in Macroalgae.

Authors:  Thillai Punitha; Siew-Moi Phang; Joon Ching Juan; John Beardall
Journal:  Mar Biotechnol (NY)       Date:  2018-04-24       Impact factor: 3.619

8.  Flavin Adenine Dinucleotide-Dependent Halogenase XanH and Engineering of Multifunctional Fusion Halogenases.

Authors:  Lingxin Kong; Qing Wang; Zixin Deng; Delin You
Journal:  Appl Environ Microbiol       Date:  2020-09-01       Impact factor: 4.792

Review 9.  Stereoselective Halogenation in Natural Product Synthesis.

Authors:  Won-jin Chung; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

10.  First-principles study of non-heme Fe(II) halogenase SyrB2 reactivity.

Authors:  Heather J Kulik; Leah C Blasiak; Nicola Marzari; Catherine L Drennan
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

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