Literature DB >> 24016264

Regioselectivity of the oxidative C-S bond formation in ergothioneine and ovothiol biosyntheses.

Heng Song1, Maureen Leninger, Norman Lee, Pinghua Liu.   

Abstract

Ergothioneine (5) and ovothiol (8) are two novel thiol-containing natural products. Their C-S bonds are formed by oxidative coupling reactions catalyzed by EgtB and OvoA enzymes, respectively. In this work, it was discovered that in addition to catalyzing the oxidative coupling between histidine and cysteine (1 → 6 conversion), OvoA can also catalyze a direct oxidative coupling between hercynine (2) and cysteine (2 → 4 conversion), which can shorten the ergothioneine biosynthetic pathway by two steps.

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Year:  2013        PMID： 24016264      PMCID： PMC4166525          DOI： 10.1021/ol402275t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  30 in total

Review 1.  Biological radical sulfur insertion reactions.

Authors:  Marc Fontecave; Sandrine Ollagnier-de-Choudens; Etienne Mulliez
Journal:  Chem Rev       Date:  2003-06       Impact factor: 60.622

2.  A dedicated glutathione S-transferase mediates carbon-sulfur bond formation in gliotoxin biosynthesis.

Authors:  Daniel H Scharf; Nicole Remme; Andreas Habel; Pranatchareeya Chankhamjon; Kirstin Scherlach; Thorsten Heinekamp; Peter Hortschansky; Axel A Brakhage; Christian Hertweck
Journal:  J Am Chem Soc       Date:  2011-07-22       Impact factor: 15.419

3.  In vitro reconstitution of Mycobacterial ergothioneine biosynthesis.

Authors:  Florian P Seebeck
Journal:  J Am Chem Soc       Date:  2010-05-19       Impact factor: 15.419

Review 4.  Novel thiols of prokaryotes.

Authors:  R C Fahey
Journal:  Annu Rev Microbiol       Date:  2001       Impact factor: 15.500

5.  Identification and characterization of the first ovothiol biosynthetic enzyme.

Authors:  Andrea Braunshausen; Florian P Seebeck
Journal:  J Am Chem Soc       Date:  2011-01-19       Impact factor: 15.419

Review 6.  Biotin synthase: insights into radical-mediated carbon-sulfur bond formation.

Authors:  Corey J Fugate; Joseph T Jarrett
Journal:  Biochim Biophys Acta       Date:  2012-01-28

7.  Model iron-oxo species and the oxidation of imidazole: insights into the mechanism of OvoA and EgtB?

Authors:  Eric A C Bushnell; Grant B Fortowsky; James W Gauld
Journal:  Inorg Chem       Date:  2012-12-05       Impact factor: 5.165

Review 8.  The structural and biochemical foundations of thiamin biosynthesis.

Authors:  Christopher T Jurgenson; Tadhg P Begley; Steven E Ealick
Journal:  Annu Rev Biochem       Date:  2009       Impact factor: 23.643

Review 9.  Lantibiotics: peptides of diverse structure and function.

Authors:  Joanne M Willey; Wilfred A van der Donk
Journal:  Annu Rev Microbiol       Date:  2007       Impact factor: 15.500

Review 10.  Self-sacrifice in radical S-adenosylmethionine proteins.

Authors:  Squire J Booker; Robert M Cicchillo; Tyler L Grove
Journal:  Curr Opin Chem Biol       Date:  2007-10       Impact factor: 8.822
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  19 in total

1.  Single-step Replacement of an Unreactive C-H Bond by a C-S Bond Using Polysulfide as the Direct Sulfur Source in Anaerobic Ergothioneine Biosynthesis.

Authors:  Ronghai Cheng; Lian Wu; Rui Lai; Chao Peng; Nathchar Naowarojna; Weiyao Hu; Xinhao Li; Stephen A Whelan; Norman Lee; Juan Lopez; Changming Zhao; Youhua Yong; Jiahui Xue; Xuefeng Jiang; Mark W Grinstaff; Zixin Deng; Jiesheng Chen; Qiang Cui; Jiahai Zhou; Pinghua Liu
Journal:  ACS Catal       Date:  2020-07-16       Impact factor: 13.084

2.  Crystal Structure of the Ergothioneine Sulfoxide Synthase from Candidatus Chloracidobacterium thermophilum and Structure-Guided Engineering To Modulate Its Substrate Selectivity.

Authors:  Nathchar Naowarojna; Seema Irani; Weiyao Hu; Ronghai Cheng; Li Zhang; Xinhao Li; Jiesheng Chen; Yan Jessie Zhang; Pinghua Liu
Journal:  ACS Catal       Date:  2019-07-02       Impact factor: 13.084

Review 3.  Go it alone: four-electron oxidations by mononuclear non-heme iron enzymes.

Authors:  Spencer C Peck; Wilfred A van der Donk
Journal:  J Biol Inorg Chem       Date:  2016-10-25       Impact factor: 3.358

4.  Implications for an imidazol-2-yl carbene intermediate in the rhodanase-catalyzed C-S bond formation reaction of anaerobic ergothioneine biosynthesis.

Authors:  Ronghai Cheng; Rui Lai; Chao Peng; Juan Lopez; Zhihong Li; Nathchar Naowarojna; Kelin Li; Christina Wong; Norman Lee; Stephen A Whelan; Lu Qiao; Mark W Grinstaff; Jiangyun Wang; Qiang Cui; Pinghua Liu
Journal:  ACS Catal       Date:  2021-03-01       Impact factor: 13.084

5.  Use of a Tyrosine Analogue To Modulate the Two Activities of a Nonheme Iron Enzyme OvoA in Ovothiol Biosynthesis, Cysteine Oxidation versus Oxidative C-S Bond Formation.

Authors:  Li Chen; Nathchar Naowarojna; Heng Song; Shu Wang; Jiangyun Wang; Zixin Deng; Changming Zhao; Pinghua Liu
Journal:  J Am Chem Soc       Date:  2018-03-21       Impact factor: 15.419

Review 6.  Mini-Review: Ergothioneine and Ovothiol Biosyntheses, an Unprecedented Trans-Sulfur Strategy in Natural Product Biosynthesis.

Authors:  Nathchar Naowarojna; Ronghai Cheng; Li Chen; Melissa Quill; Meiling Xu; Changming Zhao; Pinghua Liu
Journal:  Biochemistry       Date:  2018-04-06       Impact factor: 3.162

7.  C-S bond cleavage by a polyketide synthase domain.

Authors:  Ming Ma; Jeremy R Lohman; Tao Liu; Ben Shen
Journal:  Proc Natl Acad Sci U S A       Date:  2015-08-03       Impact factor: 11.205

8.  Electronic structures and spectroscopic signatures of diiron intermediates generated by O2 activation of nonheme iron(II)-thiolate complexes.

Authors:  Danushka M Ekanayake; Dao Pham; Andrew L Probst; Joshua R Miller; Codrina V Popescu; Adam T Fiedler
Journal:  Dalton Trans       Date:  2021-10-19       Impact factor: 4.569

9.  Mechanistic studies of a novel C-S lyase in ergothioneine biosynthesis: the involvement of a sulfenic acid intermediate.

Authors:  Heng Song; Wen Hu; Nathchar Naowarojna; Ampon Sae Her; Shu Wang; Rushil Desai; Li Qin; Xiaoping Chen; Pinghua Liu
Journal:  Sci Rep       Date:  2015-07-07       Impact factor: 4.379

10.  Nonheme iron-thiolate complexes as structural models of sulfoxide synthase active sites.

Authors:  Danushka M Ekanayake; Anne A Fischer; Maya E Elwood; Alexandra M Guzek; Sergey V Lindeman; Codrina V Popescu; Adam T Fiedler
Journal:  Dalton Trans       Date:  2020-12-22       Impact factor: 4.390
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