Literature DB >> 19675645

Mechanistic considerations of halogenating enzymes.

Alison Butler1, Moriah Sandy.   

Abstract

In nature, halogenation is a strategy used to increase the biological activity of secondary metabolites, compounds that are often effective as drugs. However, halides are not particularly reactive unless they are activated, typically by oxidation. The pace of discovery of new enzymes for halogenation is increasing, revealing new metalloenzymes, flavoenzymes, S-adenosyl-L-methionine (SAM)-dependent enzymes and others that catalyse halide oxidation using dioxygen, hydrogen peroxide and hydroperoxides, or that promote nucleophilic halide addition reactions.

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Year:  2009        PMID: 19675645     DOI: 10.1038/nature08303

Source DB:  PubMed          Journal:  Nature        ISSN: 0028-0836            Impact factor:   49.962


  49 in total

Review 1.  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

Review 2.  What's new in enzymatic halogenations.

Authors:  Danica Galonić Fujimori; Christopher T Walsh
Journal:  Curr Opin Chem Biol       Date:  2007-09-18       Impact factor: 8.822

3.  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

4.  Degradation pathway of homoserine lactone bacterial signal molecules by halogen antimicrobials identified by liquid chromatography with photodiode array and mass spectrometric detection.

Authors:  J J Michels; E J Allain; S A Borchardt; P Hu; W F McCoy
Journal:  J Chromatogr A       Date:  2000-11-17       Impact factor: 4.759

5.  Quantitating direct chlorine transfer from enzyme to substrate in chloroperoxidase-catalyzed reactions.

Authors:  R D Libby; T M Beachy; A K Phipps
Journal:  J Biol Chem       Date:  1996-09-06       Impact factor: 5.157

6.  Iodide accumulation provides kelp with an inorganic antioxidant impacting atmospheric chemistry.

Authors:  Frithjof C Küpper; Lucy J Carpenter; Gordon B McFiggans; Carl J Palmer; Tim J Waite; Eva-Maria Boneberg; Sonja Woitsch; Markus Weiller; Rafael Abela; Daniel Grolimund; Philippe Potin; Alison Butler; George W Luther; Peter M H Kroneck; Wolfram Meyer-Klaucke; Martin C Feiters
Journal:  Proc Natl Acad Sci U S A       Date:  2008-05-05       Impact factor: 11.205

7.  Substrate-triggered formation and remarkable stability of the C-H bond-cleaving chloroferryl intermediate in the aliphatic halogenase, SyrB2.

Authors:  Megan L Matthews; Courtney M Krest; Eric W Barr; Frédéric H Vaillancourt; Christopher T Walsh; Michael T Green; Carsten Krebs; J Martin Bollinger
Journal:  Biochemistry       Date:  2009-05-26       Impact factor: 3.162

8.  Methyl chloride transferase: a carbocation route for biosynthesis of halometabolites.

Authors:  A M Wuosmaa; L P Hager
Journal:  Science       Date:  1990-07-13       Impact factor: 47.728

9.  Vanadium haloperoxidase-catalyzed bromination and cyclization of terpenes.

Authors:  Jayme N Carter-Franklin; Jon D Parrish; Richard A Tschirret-Guth; R Daniel Little; Alison Butler
Journal:  J Am Chem Soc       Date:  2003-04-02       Impact factor: 15.419

Review 10.  Structural perspective on enzymatic halogenation.

Authors:  Leah C Blasiak; Catherine L Drennan
Journal:  Acc Chem Res       Date:  2009-01-20       Impact factor: 22.384

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  59 in total

1.  Iodide accumulation by aerobic bacteria isolated from subsurface sediments of a 129I-contaminated aquifer at the Savannah River site, South Carolina.

Authors:  Hsiu-Ping Li; Robin Brinkmeyer; Whitney L Jones; Saijin Zhang; Chen Xu; Kathy A Schwehr; Peter H Santschi; Daniel I Kaplan; Chris M Yeager
Journal:  Appl Environ Microbiol       Date:  2011-01-28       Impact factor: 4.792

2.  Daily bursts of biogenic cyanogen bromide (BrCN) control biofilm formation around a marine benthic diatom.

Authors:  Bart Vanelslander; Carsten Paul; Jan Grueneberg; Emily K Prince; Jeroen Gillard; Koen Sabbe; Georg Pohnert; Wim Vyverman
Journal:  Proc Natl Acad Sci U S A       Date:  2012-01-30       Impact factor: 11.205

3.  Ketone-catalyzed photochemical C(sp3)-H chlorination.

Authors:  Lei Han; Jibao Xia; Lin You; Chuo Chen
Journal:  Tetrahedron       Date:  2017-05-04       Impact factor: 2.457

Review 4.  Catalytic Mechanisms of Fe(II)- and 2-Oxoglutarate-dependent Oxygenases.

Authors:  Salette Martinez; Robert P Hausinger
Journal:  J Biol Chem       Date:  2015-07-07       Impact factor: 5.157

5.  A lifetime of playing with enzymes.

Authors:  Lowell P Hager
Journal:  J Biol Chem       Date:  2010-03-09       Impact factor: 5.157

6.  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

7.  Alison Butler: papers in celebration of her 2018 ACS Alfred Bader Award in Bioorganic or Bioinorganic Chemistry.

Authors:  Lawrence Que
Journal:  J Biol Inorg Chem       Date:  2021-05       Impact factor: 3.358

8.  Evidence That Chlorinated Auxin Is Restricted to the Fabaceae But Not to the Fabeae.

Authors:  Hong Kiat Lam; Scott A M McAdam; Erin L McAdam; John J Ross
Journal:  Plant Physiol       Date:  2015-05-13       Impact factor: 8.340

9.  The Chemistry and Biology of Nakiterpiosin - C-nor-D-Homosteroids.

Authors:  Shuanhu Gao; Qiaoling Wang; Gelin Wang; Brett Lomenick; Jie Liu; Chih-Wei Fan; Lih-Wen Deng; Jing Huang; Lawrence Lum; Chuo Chen
Journal:  Synlett       Date:  2012-10       Impact factor: 2.454

Review 10.  The halogenated metabolism of brown algae (Phaeophyta), its biological importance and its environmental significance.

Authors:  Stéphane La Barre; Philippe Potin; Catherine Leblanc; Ludovic Delage
Journal:  Mar Drugs       Date:  2010-03-31       Impact factor: 5.118

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