Repurposing Iron- and 2-Oxoglutarate-Dependent Oxygenases to Catalyze Olefin Hydration.
Biocatalysis
Hydrogen Atom Transfer
Mukaiyama Hydration
Nonheme Fe/2OG-Dependent Oxygenase
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
09 10 2023
09 10 2023
Historique:
received:
01
08
2023
pmc-release:
09
10
2024
medline:
4
10
2023
pubmed:
28
8
2023
entrez:
28
8
2023
Statut:
ppublish
Résumé
Mononuclear nonheme iron(II) and 2-oxoglutarate (Fe/2OG)-dependent oxygenases and halogenases are known to catalyze a diverse set of oxidative reactions, including hydroxylation, halogenation, epoxidation, and desaturation in primary metabolism and natural product maturation. However, their use in abiotic transformations has mainly been limited to C-H oxidation. Herein, we show that various enzymes of this family, when reconstituted with Fe(II) or Fe(III), can catalyze Mukaiyama hydration-a redox neutral transformation. Distinct from the native reactions of the Fe/2OG enzymes, wherein oxygen atom transfer (OAT) catalyzed by an iron-oxo species is involved, this nonnative transformation proceeds through a hydrogen atom transfer (HAT) pathway in a 2OG-independent manner. Additionally, in contrast to conventional inorganic catalysts, wherein a dinuclear iron species is responsible for HAT, the Fe/2OG enzymes exploit a mononuclear iron center to support this reaction. Collectively, our work demonstrates that Fe/2OG enzymes have utility in catalysis beyond the current scope of catalytic oxidation.
Identifiants
pubmed: 37639670
doi: 10.1002/anie.202311099
pmc: PMC10592062
mid: NIHMS1928274
doi:
Substances chimiques
Oxygenases
EC 1.13.-
Iron
E1UOL152H7
Ketoglutaric Acids
0
Hydrogen
7YNJ3PO35Z
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202311099Subventions
Organisme : NIGMS NIH HHS
ID : R01 GM127588
Pays : United States
Informations de copyright
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
Nat Chem Biol. 2019 Oct;15(10):1009-1016
pubmed: 31548692
J Am Chem Soc. 2006 Sep 6;128(35):11693-712
pubmed: 16939295
J Am Chem Soc. 2017 Feb 15;139(6):2484-2503
pubmed: 28094980
J Am Chem Soc. 2012 Aug 22;134(33):13588-91
pubmed: 22860624
Acc Chem Res. 2019 Apr 16;52(4):935-944
pubmed: 30912643
J Am Chem Soc. 2017 Mar 29;139(12):4306-4309
pubmed: 28291336
J Am Chem Soc. 2017 Jan 11;139(1):83-86
pubmed: 27973768
Chem Rev. 2016 Aug 10;116(15):8912-9000
pubmed: 27461578
J Am Chem Soc. 2009 Apr 8;131(13):4904-16
pubmed: 19292450
Chem Rev. 2017 Nov 8;117(21):13382-13460
pubmed: 29027792
Science. 2008 Jul 25;321(5888):572-5
pubmed: 18653896
J Biol Chem. 2021 Jan-Jun;296:100231
pubmed: 33361191
J Am Chem Soc. 2022 Apr 6;144(13):5893-5901
pubmed: 35254829
ACS Catal. 2022 Feb 18;12(4):2270-2279
pubmed: 35992736
Science. 2021 Dec 24;374(6575):1612-1616
pubmed: 34941416
Science. 2013 Nov 29;342(6162):1076-80
pubmed: 24288328
Biochemistry. 2023 Jan 17;62(2):229-240
pubmed: 35446547
Biochem Biophys Res Commun. 2009 Dec 18;390(3):506-10
pubmed: 19850012
Synlett. 2021;32(8):775-784
pubmed: 34413574
Nat Protoc. 2015 Jun;10(6):845-58
pubmed: 25950237
J Am Chem Soc. 2019 Dec 18;141(50):19585-19588
pubmed: 31790588
Angew Chem Int Ed Engl. 2016 Jan 4;55(1):422-6
pubmed: 26553478
Proc Natl Acad Sci U S A. 2017 Jul 3;114(27):7025-7030
pubmed: 28634299
Appl Environ Microbiol. 2022 May 10;88(9):e0249721
pubmed: 35435717
ACS Chem Biol. 2017 Dec 15;12(12):3067-3075
pubmed: 29131568
Proc Natl Acad Sci U S A. 2001 Oct 9;98(21):12215-20
pubmed: 11572948
Nature. 2021 Aug;596(7873):583-589
pubmed: 34265844
Cell Chem Biol. 2016 Aug 18;23(8):935-44
pubmed: 27541195
Nat Commun. 2017 Jul 19;8:16115
pubmed: 28722011
Nucleic Acids Res. 2022 Jan 7;50(D1):D439-D444
pubmed: 34791371
J Am Chem Soc. 2014 Jan 29;136(4):1300-3
pubmed: 24428640
Science. 2016 Oct 7;354(6308):102-106
pubmed: 27846500
Angew Chem Int Ed Engl. 2014 Mar 3;53(10):2730-4
pubmed: 24488606
Chem Rev. 2018 Mar 14;118(5):2491-2553
pubmed: 29286645
Inorg Chem. 2010 Apr 19;49(8):3618-28
pubmed: 20380464
Science. 2015 May 22;348(6237):886-91
pubmed: 25999503
Angew Chem Int Ed Engl. 2008;47(31):5758-60
pubmed: 18576460
Biochemistry. 1999 Nov 16;38(46):15278-86
pubmed: 10563813
Angew Chem Int Ed Engl. 2018 Feb 12;57(7):1831-1835
pubmed: 29314482
Angew Chem Int Ed Engl. 2007;46(24):4519-22
pubmed: 17479996
J Inorg Biochem. 2006 Apr;100(4):586-605
pubmed: 16513177
Science. 2003 Feb 14;299(5609):1039-42
pubmed: 12586937
Nature. 2014 Dec 18;516(7531):343-8
pubmed: 25519131
Angew Chem Int Ed Engl. 2020 May 4;59(19):7367-7371
pubmed: 32074393
J Am Chem Soc. 2015 Jul 1;137(25):8046-9
pubmed: 26088401
Angew Chem Int Ed Engl. 2014 Nov 17;53(47):12880-4
pubmed: 25251934
Science. 2013 Jan 4;339(6115):59-63
pubmed: 23288535
Nat Commun. 2015 Aug 10;6:7890
pubmed: 26259066
Chem Rev. 2018 Jan 10;118(1):142-231
pubmed: 28714313
Chem Rev. 2004 Feb;104(2):939-86
pubmed: 14871146
J Am Chem Soc. 2005 May 11;127(18):6556-62
pubmed: 15869276
Inorg Chem. 2015 Mar 2;54(5):2278-83
pubmed: 25668068
Science. 2007 Apr 20;316(5823):453-7
pubmed: 17446402
J Am Chem Soc. 2014 May 14;136(19):6884-7
pubmed: 24824195
Angew Chem Int Ed Engl. 2020 Jun 8;59(24):9478-9484
pubmed: 32160364
Trends Biochem Sci. 2018 Jul;43(7):517-532
pubmed: 29709390
Nat Chem Biol. 2014 Mar;10(3):209-15
pubmed: 24463698