Literature DB >> 22891633

A picomolar transition state analogue inhibitor of MTAN as a specific antibiotic for Helicobacter pylori.

Shanzhi Wang1, Antti M Haapalainen, Funing Yan, Quan Du, Peter C Tyler, Gary B Evans, Agnes Rinaldo-Matthis, Rosemary L Brown, Gillian E Norris, Steven C Almo, Vern L Schramm.   

Abstract

Campylobacter and Helicobacter species express a 6-amino-6-deoxyfutalosine N-ribosylhydrolase (HpMTAN) proposed to function in menaquinone synthesis. BuT-DADMe-ImmA is a 36 pM transition state analogue of HpMTAN, and the crystal structure of the enzyme-inhibitor complex reveals the mechanism of inhibition. BuT-DADMe-ImmA has a MIC(90) value of <8 ng/mL for Helicobacter pylori growth but does not cause growth arrest in other common clinical pathogens, thus demonstrating potential as an H. pylori-specific antibiotic.

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Year:  2012        PMID： 22891633      PMCID： PMC3437630          DOI： 10.1021/bi3009664

Source DB:  PubMed          Journal:  Biochemistry        ISSN： 0006-2960            Impact factor:   3.162


  21 in total

1.  A nucleosidase required for in vivo function of the S-adenosyl-L-methionine radical enzyme, biotin synthase.

Authors:  Eunjoo Choi-Rhee; John E Cronan
Journal:  Chem Biol       Date:  2005-05

2.  Picomolar inhibitors as transition-state probes of 5'-methylthioadenosine nucleosidases.

Authors:  Jemy A Gutierrez; Minkui Luo; Vipender Singh; Lei Li; Rosemary L Brown; Gillian E Norris; Gary B Evans; Richard H Furneaux; Peter C Tyler; Gavin F Painter; Dirk H Lenz; Vern L Schramm
Journal:  ACS Chem Biol       Date:  2007-11-20       Impact factor: 5.100

Review 3.  H. pylori treatment: new wine in old bottles?

Authors:  Nimish Vakil
Journal:  Am J Gastroenterol       Date:  2009-01       Impact factor: 10.864

4.  The respiratory chain of Helicobacter pylori: identification of cytochromes and the effects of oxygen on cytochrome and menaquinone levels.

Authors:  S W Marcelli; H T Chang; T Chapman; P A Chalk; R J Miles; R K Poole
Journal:  FEMS Microbiol Lett       Date:  1996-04-15       Impact factor: 2.742

5.  Transition state analogues for enzyme catalysis.

Authors:  R Wolfenden
Journal:  Nature       Date:  1969-08-16       Impact factor: 49.962

6.  Transition state structure of 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase from Escherichia coli and its similarity to transition state analogues.

Authors:  Vipender Singh; Jeffrey E Lee; Sara Núñez; P Lynne Howell; Vern L Schramm
Journal:  Biochemistry       Date:  2005-09-06       Impact factor: 3.162

7.  Transition-state analysis of S. pneumoniae 5'-methylthioadenosine nucleosidase.

Authors:  Vipender Singh; Vern L Schramm
Journal:  J Am Chem Soc       Date:  2007-02-14       Impact factor: 15.419

8.  Femtomolar transition state analogue inhibitors of 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase from Escherichia coli.

Authors:  Vipender Singh; Gary B Evans; Dirk H Lenz; Jennifer M Mason; Keith Clinch; Simon Mee; Gavin F Painter; Peter C Tyler; Richard H Furneaux; Jeffrey E Lee; P Lynne Howell; Vern L Schramm
Journal:  J Biol Chem       Date:  2005-03-04       Impact factor: 5.157

9.  Vitamin K (menaquinone) biosynthesis in bacteria: high-performance liquid chromatographic assay of the overall synthesis of o-succinylbenzoic acid and of 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylic acid synthase.

Authors:  J L Popp; C Berliner; R Bentley
Journal:  Anal Biochem       Date:  1989-05-01       Impact factor: 3.365

Review 10.  The prevalence of Helicobacter pylori in peptic ulcer disease.

Authors:  E J Kuipers; J C Thijs; H P Festen
Journal:  Aliment Pharmacol Ther       Date:  1995       Impact factor: 8.171
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  26 in total

1.  Identification of tirandamycins as specific inhibitors of the futalosine pathway.

Authors:  Yasushi Ogasawara; Kensuke Kondo; Ayumi Ikeda; Rikako Harada; Tohru Dairi
Journal:  J Antibiot (Tokyo)       Date:  2017-03-01       Impact factor: 2.649

2.  Continuous Fluorescence Assays for Reactions Involving Adenine.

Authors:  Ross S Firestone; Scott A Cameron; Peter C Tyler; Rodrigo G Ducati; Adam Z Spitz; Vern L Schramm
Journal:  Anal Chem       Date:  2016-11-11       Impact factor: 6.986

3.  Crystal structures of the Helicobacter pylori MTAN enzyme reveal specific interactions between S-adenosylhomocysteine and the 5'-alkylthio binding subsite.

Authors:  Vidhi Mishra; Donald R Ronning
Journal:  Biochemistry       Date:  2012-11-20       Impact factor: 3.162

4.  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

5.  Structural and biochemical characterization of Chlamydia trachomatis hypothetical protein CT263 supports that menaquinone synthesis occurs through the futalosine pathway.

Authors:  Michael L Barta; Keisha Thomas; Hongling Yuan; Scott Lovell; Kevin P Battaile; Vern L Schramm; P Scott Hefty
Journal:  J Biol Chem       Date:  2014-09-24       Impact factor: 5.157

6.  Neutron structures of the Helicobacter pylori 5'-methylthioadenosine nucleosidase highlight proton sharing and protonation states.

Authors:  Michael T Banco; Vidhi Mishra; Andreas Ostermann; Tobias E Schrader; Gary B Evans; Andrey Kovalevsky; Donald R Ronning
Journal:  Proc Natl Acad Sci U S A       Date:  2016-11-16       Impact factor: 11.205

7.  Transition State Analogue Inhibitors of 5'-Deoxyadenosine/5'-Methylthioadenosine Nucleosidase from Mycobacterium tuberculosis.

Authors:  Hilda A Namanja-Magliano; Gary B Evans; Rajesh K Harijan; Peter C Tyler; Vern L Schramm
Journal:  Biochemistry       Date:  2017-09-07       Impact factor: 3.162

Review 8.  Transition States, analogues, and drug development.

Authors:  Vern L Schramm
Journal:  ACS Chem Biol       Date:  2013-01-04       Impact factor: 5.100

9.  Molecular dynamics study of the effect of active site protonation on Helicobacter pylori 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase.

Authors:  Mustafa Tekpinar; Ahmet Yildirim; Tsjerk A Wassenaar
Journal:  Eur Biophys J       Date:  2015-08-08       Impact factor: 1.733

10.  Salmonella enterica MTAN at 1.36 Å resolution: a structure-based design of tailored transition state analogs.

Authors:  Antti M Haapalainen; Keisha Thomas; Peter C Tyler; Gary B Evans; Steven C Almo; Vern L Schramm
Journal:  Structure       Date:  2013-05-16       Impact factor: 5.006
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