Literature DB >> 25477515

Radical S-adenosylmethionine (SAM) enzymes in cofactor biosynthesis: a treasure trove of complex organic radical rearrangement reactions.

Angad P Mehta1, Sameh H Abdelwahed1, Nilkamal Mahanta1, Dmytro Fedoseyenko1, Benjamin Philmus1, Lisa E Cooper1, Yiquan Liu1, Isita Jhulki1, Steven E Ealick2, Tadhg P Begley3.   

Abstract

In this minireview, we describe the radical S-adenosylmethionine enzymes involved in the biosynthesis of thiamin, menaquinone, molybdopterin, coenzyme F420, and heme. Our focus is on the remarkably complex organic rearrangements involved, many of which have no precedent in organic or biological chemistry.
© 2015 by The American Society for Biochemistry and Molecular Biology, Inc.

Entities:  

Keywords:  Biosynthesis; Deazaflavin; Enzyme Mechanism; Heme; Menaquinone; Molybdopterin; Rearrangement; S-Adenosylmethionine (SAM); Thiamin; radical

Mesh:

Substances:

Year:  2014        PMID: 25477515      PMCID: PMC4326808          DOI: 10.1074/jbc.R114.623793

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


  39 in total

1.  Crystal structure of coproporphyrinogen III oxidase reveals cofactor geometry of Radical SAM enzymes.

Authors:  Gunhild Layer; Jürgen Moser; Dirk W Heinz; Dieter Jahn; Wolf-Dieter Schubert
Journal:  EMBO J       Date:  2003-12-01       Impact factor: 11.598

Review 2.  Convergent strategies in biosynthesis.

Authors:  Tohru Dairi; Tomohisa Kuzuyama; Makoto Nishiyama; Isao Fujii
Journal:  Nat Prod Rep       Date:  2011-05-06       Impact factor: 13.423

3.  Identification of a cyclic nucleotide as a cryptic intermediate in molybdenum cofactor biosynthesis.

Authors:  Bradley M Hover; Anna Loksztejn; Anthony A Ribeiro; Kenichi Yokoyama
Journal:  J Am Chem Soc       Date:  2013-04-29       Impact factor: 15.419

4.  The HydG enzyme generates an Fe(CO)2(CN) synthon in assembly of the FeFe hydrogenase H-cluster.

Authors:  Jon M Kuchenreuther; William K Myers; Daniel L M Suess; Troy A Stich; Vladimir Pelmenschikov; Stacey A Shiigi; Stephen P Cramer; James R Swartz; R David Britt; Simon J George
Journal:  Science       Date:  2014-01-24       Impact factor: 47.728

5.  Anaerobic and aerobic coproporphyrinogen III oxidases of Rhodopseudomonas spheroides. Mechanism and stereochemistry of vinyl group formation.

Authors:  J S Seehra; P M Jordan; M Akhtar
Journal:  Biochem J       Date:  1983-03-01       Impact factor: 3.857

Review 6.  Radicals from S-adenosylmethionine and their application to biosynthesis.

Authors:  Peter L Roach
Journal:  Curr Opin Chem Biol       Date:  2010-12-13       Impact factor: 8.822

Review 7.  The biosynthesis of thiol- and thioether-containing cofactors and secondary metabolites catalyzed by radical S-adenosylmethionine enzymes.

Authors:  Joseph T Jarrett
Journal:  J Biol Chem       Date:  2014-12-04       Impact factor: 5.157

8.  The History of the Discovery of the Molybdenum Cofactor and Novel Aspects of its Biosynthesis in Bacteria.

Authors:  Silke Leimkühler; Margot M Wuebbens; K V Rajagopalan
Journal:  Coord Chem Rev       Date:  2011-05-01       Impact factor: 22.315

9.  Biosynthesis of F0, precursor of the F420 cofactor, requires a unique two radical-SAM domain enzyme and tyrosine as substrate.

Authors:  Laure Decamps; Benjamin Philmus; Alhosna Benjdia; Robert White; Tadhg P Begley; Olivier Berteau
Journal:  J Am Chem Soc       Date:  2012-10-24       Impact factor: 15.419

10.  Menaquinone biosynthesis: formation of aminofutalosine requires a unique radical SAM enzyme.

Authors:  Nilkamal Mahanta; Dmytro Fedoseyenko; Tohru Dairi; Tadhg P Begley
Journal:  J Am Chem Soc       Date:  2013-10-07       Impact factor: 15.419

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  23 in total

Review 1.  Enzymatic Cascade Reactions in Biosynthesis.

Authors:  Christopher T Walsh; Bradley S Moore
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-20       Impact factor: 15.336

2.  Antibacterial Strategy against H. pylori: Inhibition of the Radical SAM Enzyme MqnE in Menaquinone Biosynthesis.

Authors:  Sumedh Joshi; Dmytro Fedoseyenko; Nilkamal Mahanta; Rodrigo G Ducati; Mu Feng; Vern L Schramm; Tadhg P Begley
Journal:  ACS Med Chem Lett       Date:  2019-02-15       Impact factor: 4.345

3.  Theory and Application of the Relationship Between Steady-State Isotope Effects on Enzyme Intermediate Concentrations and Net Rate Constants.

Authors:  Mark W Ruszczycky; Hung-Wen Liu
Journal:  Methods Enzymol       Date:  2017-08-31       Impact factor: 1.600

4.  Highly regulated, diversifying NTP-dependent biological conflict systems with implications for the emergence of multicellularity.

Authors:  Gurmeet Kaur; A Maxwell Burroughs; Lakshminarayan M Iyer; L Aravind
Journal:  Elife       Date:  2020-02-26       Impact factor: 8.140

Review 5.  Recent Advances in Enzymatic Complexity Generation: Cyclization Reactions.

Authors:  Christopher T Walsh; Yi Tang
Journal:  Biochemistry       Date:  2017-12-20       Impact factor: 3.162

6.  Mechanistic Studies on Tryptophan Lyase (NosL): Identification of Cyanide as a Reaction Product.

Authors:  Dhananjay M Bhandari; Dmytro Fedoseyenko; Tadhg P Begley
Journal:  J Am Chem Soc       Date:  2018-01-02       Impact factor: 15.419

7.  The radical SAM protein HemW is a heme chaperone.

Authors:  Vera Haskamp; Simone Karrie; Toni Mingers; Stefan Barthels; François Alberge; Axel Magalon; Katrin Müller; Eckhard Bill; Wolfgang Lubitz; Kirstin Kleeberg; Peter Schweyen; Martin Bröring; Martina Jahn; Dieter Jahn
Journal:  J Biol Chem       Date:  2017-12-27       Impact factor: 5.157

Review 8.  Radical S-Adenosylmethionine Enzymes Involved in RiPP Biosynthesis.

Authors:  Nilkamal Mahanta; Graham A Hudson; Douglas A Mitchell
Journal:  Biochemistry       Date:  2017-09-22       Impact factor: 3.162

Review 9.  Following the electrons: peculiarities in the catalytic cycles of radical SAM enzymes.

Authors:  Mark W Ruszczycky; Aoshu Zhong; Hung-Wen Liu
Journal:  Nat Prod Rep       Date:  2018-07-18       Impact factor: 13.423

10.  New Insight into the Mechanism of Anaerobic Heme Degradation.

Authors:  Liju G Mathew; Nathaniel R Beattie; Clayton Pritchett; William N Lanzilotta
Journal:  Biochemistry       Date:  2019-11-07       Impact factor: 3.162

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