Literature DB >> 16195462

Tryptophan 7-halogenase (PrnA) structure suggests a mechanism for regioselective chlorination.

Changjiang Dong1, Silvana Flecks, Susanne Unversucht, Caroline Haupt, Karl-Heinz van Pée, James H Naismith.   

Abstract

Chlorinated natural products include vancomycin and cryptophycin A. Their biosynthesis involves regioselective chlorination by flavin-dependent halogenases. We report the structural characterization of tryptophan 7-halogenase (PrnA), which regioselectively chlorinates tryptophan. Tryptophan and flavin adenine dinucleotide (FAD) are separated by a 10 angstrom-long tunnel and bound by distinct enzyme modules. The FAD module is conserved in halogenases and is related to flavin-dependent monooxygenases. On the basis of biochemical studies, crystal structures, and by analogy with monooxygenases, we predict that FADH2 reacts with O2 to make peroxyflavin, which is decomposed by Cl-. The resulting HOCl is guided through the tunnel to tryptophan, where it is activated to participate in electrophilic aromatic substitution.

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Year:  2005        PMID： 16195462      PMCID： PMC3315827          DOI： 10.1126/science.1116510

Source DB:  PubMed          Journal:  Science        ISSN： 0036-8075            Impact factor:   47.728


  27 in total

1.  Molecular cloning and sequence analysis of the complestatin biosynthetic gene cluster.

Authors:  H T Chiu; B K Hubbard; A N Shah; J Eide; R A Fredenburg; C T Walsh; C Khosla
Journal:  Proc Natl Acad Sci U S A       Date:  2001-07-10       Impact factor: 11.205

2.  Clorobiocin biosynthesis in Streptomyces: identification of the halogenase and generation of structural analogs.

Authors:  Alessandra S Eustáquio; Bertolt Gust; Thomas Luft; Shu Ming Li; Keith F Chater; Lutz Heide
Journal:  Chem Biol       Date:  2003-03

3.  Biosynthesis of the orthosomycin antibiotic avilamycin A: deductions from the molecular analysis of the avi biosynthetic gene cluster of Streptomyces viridochromogenes Tü57 and production of new antibiotics.

Authors:  G Weitnauer; A Mühlenweg; A Trefzer; D Hoffmeister; R D Süssmuth; G Jung; K Welzel; A Vente; U Girreser; A Bechthold
Journal:  Chem Biol       Date:  2001-06

4.  Conservation of the pyrrolnitrin biosynthetic gene cluster among six pyrrolnitrin-producing strains.

Authors:  P E Hammer; W Burd; D S Hill; J M Ligon; K van Pée
Journal:  FEMS Microbiol Lett       Date:  1999-11-01       Impact factor: 2.742

5.  Mechanistic studies of cyclohexanone monooxygenase: chemical properties of intermediates involved in catalysis.

Authors:  D Sheng; D P Ballou; V Massey
Journal:  Biochemistry       Date:  2001-09-18       Impact factor: 3.162

6.  Cloning and nucleotide sequence of the gene responsible for chlorination of tetracycline.

Authors:  T Dairi; T Nakano; K Aisaka; R Katsumata; M Hasegawa
Journal:  Biosci Biotechnol Biochem       Date:  1995-06       Impact factor: 2.043

7.  Comparison of the three-dimensional protein and nucleotide structure of the FAD-binding domain of p-hydroxybenzoate hydroxylase with the FAD- as well as NADPH-binding domains of glutathione reductase.

Authors:  R K Wierenga; J Drenth; G E Schulz
Journal:  J Mol Biol       Date:  1983-07-05       Impact factor: 5.469

8.  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

Review 9.  Vancomycin assembly: nature's way.

Authors:  Brian K Hubbard; Christopher T Walsh
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-17       Impact factor: 15.336

10.  Flavin-oxygen derivatives involved in hydroxylation by p-hydroxybenzoate hydroxylase.

Authors:  B Entsch; D P Ballou; V Massey
Journal:  J Biol Chem       Date:  1976-05-10       Impact factor: 5.157
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  96 in total

1.  Function and Structure of MalA/MalA', Iterative Halogenases for Late-Stage C-H Functionalization of Indole Alkaloids.

Authors:  Amy E Fraley; Marc Garcia-Borràs; Ashootosh Tripathi; Dheeraj Khare; Eduardo V Mercado-Marin; Hong Tran; Qingyun Dan; Gabrielle P Webb; Katharine R Watts; Phillip Crews; Richmond Sarpong; Robert M Williams; Janet L Smith; K N Houk; David H Sherman
Journal:  J Am Chem Soc       Date:  2017-08-21       Impact factor: 15.419

2.  pH-dependent studies reveal an efficient hydroxylation mechanism of the oxygenase component of p-hydroxyphenylacetate 3-hydroxylase.

Authors:  Nantidaporn Ruangchan; Chanakan Tongsook; Jeerus Sucharitakul; Pimchai Chaiyen
Journal:  J Biol Chem       Date:  2010-10-28       Impact factor: 5.157

3.  Biosynthesis of l-4-Chlorokynurenine, an Antidepressant Prodrug and a Non-Proteinogenic Amino Acid Found in Lipopeptide Antibiotics.

Authors:  Hanna Luhavaya; Renata Sigrist; Jonathan R Chekan; Shaun M K McKinnie; Bradley S Moore
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-13       Impact factor: 15.336

Review 4.  Dynamics and mechanisms of DNA repair by photolyase.

Authors:  Zheyun Liu; Lijuan Wang; Dongping Zhong
Journal:  Phys Chem Chem Phys       Date:  2015-05-14       Impact factor: 3.676

Review 5.  Halogenase engineering and its utility in medicinal chemistry.

Authors:  Amy E Fraley; David H Sherman
Journal:  Bioorg Med Chem Lett       Date:  2018-04-30       Impact factor: 2.823

6.  The purification, crystallization and preliminary structural characterization of FAD-dependent monooxygenase PhzS, a phenazine-modifying enzyme from Pseudomonas aeruginosa.

Authors:  Neelakshi Gohain; Linda S Thomashow; Dmitri V Mavrodi; Wulf Blankenfeldt
Journal:  Acta Crystallogr Sect F Struct Biol Cryst Commun       Date:  2006-09-30

7.  Structure of the monooxygenase component of a two-component flavoprotein monooxygenase.

Authors:  Andrea Alfieri; Francesco Fersini; Nantidaporn Ruangchan; Methinee Prongjit; Pimchai Chaiyen; Andrea Mattevi
Journal:  Proc Natl Acad Sci U S A       Date:  2007-01-16       Impact factor: 11.205

8.  Mechanism of enzymatic fluorination in Streptomyces cattleya.

Authors:  Xiaofeng Zhu; David A Robinson; Andrew R McEwan; David O'Hagan; James H Naismith
Journal:  J Am Chem Soc       Date:  2007-11-07       Impact factor: 15.419

9.  Characterization of PlGoxB, a flavoprotein required for cysteine tryptophylquinone biosynthesis in glycine oxidase from Pseudoalteromonas luteoviolacea.

Authors:  Kyle J Mamounis; Zhongxin Ma; Antonio Sanchez-Amat; Victor L Davidson
Journal:  Arch Biochem Biophys       Date:  2019-09-18       Impact factor: 4.013

10.  Detection, distribution, and organohalogen compound discovery implications of the reduced flavin adenine dinucleotide-dependent halogenase gene in major filamentous actinomycete taxonomic groups.

Authors:  Peng Gao; Ying Huang
Journal:  Appl Environ Microbiol       Date:  2009-05-15       Impact factor: 4.792
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