Literature DB >> 26152721

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

Salette Martinez1, Robert P Hausinger2.   

Abstract

Mononuclear non-heme Fe(II)- and 2-oxoglutarate (2OG)-dependent oxygenases comprise a large family of enzymes that utilize an Fe(IV)-oxo intermediate to initiate diverse oxidative transformations with important biological roles. Here, four of the major types of Fe(II)/2OG-dependent reactions are detailed: hydroxylation, halogenation, ring formation, and desaturation. In addition, an atypical epimerization reaction is described. Studies identifying several key intermediates in catalysis are concisely summarized, and the proposed mechanisms are explained. In addition, a variety of other transformations catalyzed by selected family members are briefly described to further highlight the chemical versatility of these enzymes.
© 2015 by The American Society for Biochemistry and Molecular Biology, Inc.

Entities:  

Keywords:  2-oxoglutarate; desaturation; dioxygenase; enzyme mechanism; halogenase; hydroxylase; iron; metalloenzyme; ring-formation

Mesh:

Substances:

Year:  2015        PMID: 26152721      PMCID: PMC4543632          DOI: 10.1074/jbc.R115.648691

Source DB:  PubMed          Journal:  J Biol Chem        ISSN: 0021-9258            Impact factor:   5.157


  79 in total

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Journal:  J Biol Chem       Date:  2013-02-28       Impact factor: 5.157

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Journal:  Annu Rev Biochem       Date:  2014       Impact factor: 23.643

3.  Insight into the mechanism of an iron dioxygenase by resolution of steps following the FeIV=HO species.

Authors:  Piotr K Grzyska; Evan H Appelman; Robert P Hausinger; Denis A Proshlyakov
Journal:  Proc Natl Acad Sci U S A       Date:  2010-02-10       Impact factor: 11.205

4.  X-ray crystal structure of Escherichia coli taurine/alpha-ketoglutarate dioxygenase complexed to ferrous iron and substrates.

Authors:  Jonathan M Elkins; Matthew J Ryle; Ian J Clifton; Julie C Dunning Hotopp; John S Lloyd; Nicolai I Burzlaff; Jack E Baldwin; Robert P Hausinger; Peter L Roach
Journal:  Biochemistry       Date:  2002-04-23       Impact factor: 3.162

5.  Mechanism of dioxygen activation in 2-oxoglutarate-dependent enzymes: a hybrid DFT study.

Authors:  Tomasz Borowski; Arianna Bassan; Per E M Siegbahn
Journal:  Chemistry       Date:  2004-02-20       Impact factor: 5.236

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

Authors:  Matthew L Hillwig; Xinyu Liu
Journal:  Nat Chem Biol       Date:  2014-09-14       Impact factor: 15.040

7.  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

8.  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

Review 9.  Structural studies on 2-oxoglutarate oxygenases and related double-stranded beta-helix fold proteins.

Authors:  Ian J Clifton; Michael A McDonough; Dominic Ehrismann; Nadia J Kershaw; Nicolas Granatino; Christopher J Schofield
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10.  The role of chloride in the mechanism of O(2) activation at the mononuclear nonheme Fe(II) center of the halogenase HctB.

Authors:  Sarah M Pratter; Kenneth M Light; Edward I Solomon; Grit D Straganz
Journal:  J Am Chem Soc       Date:  2014-06-16       Impact factor: 15.419

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  117 in total

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Authors:  Noah P Dunham; Wei-Chen Chang; Andrew J Mitchell; Ryan J Martinie; Bo Zhang; Jonathan A Bergman; Lauren J Rajakovich; Bo Wang; Alexey Silakov; Carsten Krebs; Amie K Boal; J Martin Bollinger
Journal:  J Am Chem Soc       Date:  2018-06-04       Impact factor: 15.419

Review 2.  Introduction: Metals in Biology: α-Ketoglutarate/Iron-Dependent Dioxygenases.

Authors:  F Peter Guengerich
Journal:  J Biol Chem       Date:  2015-07-07       Impact factor: 5.157

3.  Pathway from N-Alkylglycine to Alkylisonitrile Catalyzed by Iron(II) and 2-Oxoglutarate-Dependent Oxygenases.

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4.  Discovery of Hydroxylase Activity for PqqB Provides a Missing Link in the Pyrroloquinoline Quinone Biosynthetic Pathway.

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5.  Evidence that oxidative dephosphorylation by the nonheme Fe(II), α-ketoglutarate:UMP oxygenase occurs by stereospecific hydroxylation.

Authors:  Anwesha Goswami; Xiaodong Liu; Wenlong Cai; Thomas P Wyche; Tim S Bugni; Maïa Meurillon; Suzanne Peyrottes; Christian Perigaud; Koichi Nonaka; Jürgen Rohr; Steven G Van Lanen
Journal:  FEBS Lett       Date:  2017-01-25       Impact factor: 4.124

Review 6.  Oxidative Cyclization in Natural Product Biosynthesis.

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Review 7.  The Metal Drives the Chemistry: Dual Functions of Acireductone Dioxygenase.

Authors:  Aditi R Deshpande; Thomas C Pochapsky; Dagmar Ringe
Journal:  Chem Rev       Date:  2017-07-21       Impact factor: 60.622

8.  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

9.  Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine.

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10.  Evaluation of a concerted vs. sequential oxygen activation mechanism in α-ketoglutarate-dependent nonheme ferrous enzymes.

Authors:  Serra Goudarzi; Shyam R Iyer; Jeffrey T Babicz; James J Yan; Günther H J Peters; Hans E M Christensen; Britt Hedman; Keith O Hodgson; Edward I Solomon
Journal:  Proc Natl Acad Sci U S A       Date:  2020-02-24       Impact factor: 11.205

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