Literature DB >> 25218740

A new family of iron-dependent halogenases acts on freestanding substrates.

Matthew L Hillwig1, Xinyu Liu1.   

Abstract

Regio- and stereospecific incorporation of a halogen atom to an unactivated sp(3) carbon in a freestanding molecule is a challenging transformation that is currently missing in the inventory of enzyme-mediated reactions. Here we report what is to our knowledge the first example of a nonheme iron enzyme (WelO5) in the welwitindolinone biosynthetic pathway that can monochlorinate an aliphatic carbon in 12-epi-fischerindole U and 12-epi-hapalindole C, substrates that are free from peptidyl or acyl carrier protein.

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Year:  2014        PMID： 25218740     DOI： 10.1038/nchembio.1625

Source DB:  PubMed          Journal:  Nat Chem Biol        ISSN： 1552-4450            Impact factor:   15.040


  20 in total

1.  Enzymatic generation of the antimetabolite gamma,gamma-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete.

Authors:  Masashi Ueki; Danica P Galonić; Frédéric H Vaillancourt; Sylvie Garneau-Tsodikova; Ellen Yeh; David A Vosburg; Frank C Schroeder; Hiroyuki Osada; Christopher T Walsh
Journal:  Chem Biol       Date:  2006-11

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.  SyrB2 in syringomycin E biosynthesis is a nonheme FeII alpha-ketoglutarate- and O2-dependent halogenase.

Authors:  Frédéric H Vaillancourt; Jun Yin; Christopher T Walsh
Journal:  Proc Natl Acad Sci U S A       Date:  2005-07-07       Impact factor: 11.205

Review 4.  Diversity of P450 enzymes in the biosynthesis of natural products.

Authors:  Larissa M Podust; David H Sherman
Journal:  Nat Prod Rep       Date:  2012-07-23       Impact factor: 13.423

5.  New cytotoxic salinosporamides from the marine Actinomycete Salinispora tropica.

Authors:  Philip G Williams; Greg O Buchanan; Robert H Feling; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal:  J Org Chem       Date:  2005-08-05       Impact factor: 4.354

6.  Substrate positioning controls the partition between halogenation and hydroxylation in the aliphatic halogenase, SyrB2.

Authors:  Megan L Matthews; Christopher S Neumann; Linde A Miles; Tyler L Grove; Squire J Booker; Carsten Krebs; Christopher T Walsh; J Martin Bollinger
Journal:  Proc Natl Acad Sci U S A       Date:  2009-10-06       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.  Biosynthesis of ambiguine indole alkaloids in cyanobacterium Fischerella ambigua.

Authors:  Matthew L Hillwig; Qin Zhu; Xinyu Liu
Journal:  ACS Chem Biol       Date:  2013-11-20       Impact factor: 5.100

9.  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

10.  A flavin-dependent halogenase catalyzes the chlorination step in the biosynthesis of Dictyostelium differentiation-inducing factor 1.

Authors:  Christopher S Neumann; Christopher T Walsh; Robert R Kay
Journal:  Proc Natl Acad Sci U S A       Date:  2010-03-15       Impact factor: 11.205
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  38 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.  Assembly of the unusual oxacycles in the orthosomycin antibiotics.

Authors:  Amie K Boal; J Martin Bollinger; Wei-chen Chang
Journal:  Proc Natl Acad Sci U S A       Date:  2015-09-16       Impact factor: 11.205

Review 3.  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

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 Fivefold Parallelized Biosynthetic Process Secures Chlorination of Armillaria mellea (Honey Mushroom) Toxins.

Authors:  Jonas Wick; Daniel Heine; Gerald Lackner; Mathias Misiek; James Tauber; Hans Jagusch; Christian Hertweck; Dirk Hoffmeister
Journal:  Appl Environ Microbiol       Date:  2015-12-11       Impact factor: 4.792

6.  Enzymology: A radical finding.

Authors:  Rebecca J M Goss; Sabine Grüschow
Journal:  Nat Chem Biol       Date:  2014-09-14       Impact factor: 15.040

7.  Engineered Production of Hapalindole Alkaloids in the Cyanobacterium Synechococcus sp. UTEX 2973.

Authors:  Cory J Knoot; Yogan Khatri; Robert M Hohlman; David H Sherman; Himadri B Pakrasi
Journal:  ACS Synth Biol       Date:  2019-07-19       Impact factor: 5.110

8.  Hapalindole/Ambiguine Biogenesis Is Mediated by a Cope Rearrangement, C-C Bond-Forming Cascade.

Authors:  Shasha Li; Andrew N Lowell; Fengan Yu; Avi Raveh; Sean A Newmister; Nathan Bair; Jeffrey M Schaub; Robert M Williams; David H Sherman
Journal:  J Am Chem Soc       Date:  2015-12-02       Impact factor: 15.419

9.  Determining the Inherent Selectivity for Carbon Radical Hydroxylation versus Halogenation with FeIII(OH)(X) Complexes: Relevance to the Rebound Step in Non-heme Iron Halogenases.

Authors:  Vishal Yadav; Rodolfo J Rodriguez; Maxime A Siegler; David P Goldberg
Journal:  J Am Chem Soc       Date:  2020-04-13       Impact factor: 15.419

10.  Unified biogenesis of ambiguine, fischerindole, hapalindole and welwitindolinone: identification of a monogeranylated indolenine as a cryptic common biosynthetic intermediate by an unusual magnesium-dependent aromatic prenyltransferase.

Authors:  Xinyu Liu; Matthew L Hillwig; Leonardus M I Koharudin; Angela M Gronenborn
Journal:  Chem Commun (Camb)       Date:  2016-01-07       Impact factor: 6.222
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