Literature DB >> 21738918

Simple synthesis of 1,3-cyclopentanedione derived probes for labeling sulfenic acid proteins.

Jiang Qian1, Chananat Klomsiri, Marcus W Wright, S Bruce King, Allen W Tsang, Leslie B Poole, Cristina M Furdui.   

Abstract

Facile, two-step synthesis and kinetic characterization of new chemical probes for selective labeling of sulfenic acid (-SOH) in proteins are presented. The synthesis route relies on the simple and highly efficient Michael addition of thiol containing tags or linkers to 4-cyclopentene-1,3-dione, the unsaturated derivative of 1,3-cyclopentanedione.

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Year:  2011        PMID： 21738918      PMCID： PMC3587177          DOI： 10.1039/c1cc12127h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  18 in total

1.  Isoform-specific regulation of Akt by PDGF-induced reactive oxygen species.

Authors:  Revati Wani; Jiang Qian; Leimiao Yin; Erika Bechtold; S Bruce King; Leslie B Poole; Eunok Paek; Allen W Tsang; Cristina M Furdui
Journal:  Proc Natl Acad Sci U S A       Date:  2011-06-13       Impact factor: 11.205

2.  Redox-based probes for protein tyrosine phosphatases.

Authors:  Stephen E Leonard; Francisco J Garcia; David S Goodsell; Kate S Carroll
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-18       Impact factor: 15.336

3.  The inactivation of the acyl phosphatase activity catalyzed by the sulfenic acid form of glyceraldehyde 3-phosphate dehydrogenase by dimedone and olefins.

Authors:  L V Benitez; W S Allison
Journal:  J Biol Chem       Date:  1974-10-10       Impact factor: 5.157

4.  Synthesis of chemical probes to map sulfenic acid modifications on proteins.

Authors:  Leslie B Poole; Bu-Bing Zeng; Sarah A Knaggs; Mamudu Yakubu; S Bruce King
Journal:  Bioconjug Chem       Date:  2005 Nov-Dec       Impact factor: 4.774

Review 5.  Sulfenic acids as reactive intermediates in xenobiotic metabolism.

Authors:  Daniel Mansuy; Patrick M Dansette
Journal:  Arch Biochem Biophys       Date:  2010-10-01       Impact factor: 4.013

6.  Widespread sulfenic acid formation in tissues in response to hydrogen peroxide.

Authors:  Adrian T Saurin; Hendrik Neubert; Jonathan P Brennan; Philip Eaton
Journal:  Proc Natl Acad Sci U S A       Date:  2004-12-16       Impact factor: 11.205

Review 7.  Use of dimedone-based chemical probes for sulfenic acid detection evaluation of conditions affecting probe incorporation into redox-sensitive proteins.

Authors:  Chananat Klomsiri; Kimberly J Nelson; Erika Bechtold; Laura Soito; Lynnette C Johnson; W Todd Lowther; Seong-Eon Ryu; S Bruce King; Cristina M Furdui; Leslie B Poole
Journal:  Methods Enzymol       Date:  2010       Impact factor: 1.600

8.  Redox regulation of protein tyrosine phosphatase 1B involves a sulphenyl-amide intermediate.

Authors:  Annette Salmeen; Jannik N Andersen; Michael P Myers; Tzu-Ching Meng; John A Hinks; Nicholas K Tonks; David Barford
Journal:  Nature       Date:  2003-06-12       Impact factor: 49.962

9.  Protein modification, bioconjugation, and disulfide bridging using bromomaleimides.

Authors:  Mark E B Smith; Felix F Schumacher; Chris P Ryan; Lauren M Tedaldi; Danai Papaioannou; Gabriel Waksman; Stephen Caddick; James R Baker
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

10.  Protein sulfenation as a redox sensor: proteomics studies using a novel biotinylated dimedone analogue.

Authors:  Rebecca L Charles; Ewald Schröder; Georgina May; Paul Free; Piers R J Gaffney; Robin Wait; Shajna Begum; Richard J Heads; Philip Eaton
Journal:  Mol Cell Proteomics       Date:  2007-06-14       Impact factor: 5.911
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  30 in total

Review 1.  Effects of ionizing radiation on biological molecules--mechanisms of damage and emerging methods of detection.

Authors:  Julie A Reisz; Nidhi Bansal; Jiang Qian; Weiling Zhao; Cristina M Furdui
Journal:  Antioxid Redox Signal       Date:  2014-02-21       Impact factor: 8.401

Review 2.  Chemical approaches to detect and analyze protein sulfenic acids.

Authors:  Cristina M Furdui; Leslie B Poole
Journal:  Mass Spectrom Rev       Date:  2013-09-17       Impact factor: 10.946

3.  Chemoselective ratiometric imaging of protein S-sulfenylation.

Authors:  Christopher T M B Tom; John E Crellin; Hashim F Motiwala; Matthew B Stone; Dahvid Davda; William Walker; Yu-Hsuan Kuo; Jeannie L Hernandez; Kristin J Labby; Lyanne Gomez-Rodriguez; Paul M Jenkins; Sarah L Veatch; Brent R Martin
Journal:  Chem Commun (Camb)       Date:  2017-06-29       Impact factor: 6.222

4.  Peroxide-Dependent MGL Sulfenylation Regulates 2-AG-Mediated Endocannabinoid Signaling in Brain Neurons.

Authors:  Emmanuel Y Dotsey; Kwang-Mook Jung; Abdul Basit; Don Wei; Jennifer Daglian; Federica Vacondio; Andrea Armirotti; Marco Mor; Daniele Piomelli
Journal:  Chem Biol       Date:  2015-05-21

Review 5.  Mass spectrometry in studies of protein thiol chemistry and signaling: opportunities and caveats.

Authors:  Nelmi O Devarie Baez; Julie A Reisz; Cristina M Furdui
Journal:  Free Radic Biol Med       Date:  2014-09-28       Impact factor: 7.376

Review 6.  Cysteine-mediated redox signaling: chemistry, biology, and tools for discovery.

Authors:  Candice E Paulsen; Kate S Carroll
Journal:  Chem Rev       Date:  2013-03-20       Impact factor: 60.622

7.  A simple and effective strategy for labeling cysteine sulfenic acid in proteins by utilization of β-ketoesters as cleavable probes.

Authors:  Jiang Qian; Revati Wani; Chananat Klomsiri; Leslie B Poole; Allen W Tsang; Cristina M Furdui
Journal:  Chem Commun (Camb)       Date:  2012-03-20       Impact factor: 6.222

8.  Introduction to approaches and tools for the evaluation of protein cysteine oxidation.

Authors:  Leslie B Poole; Cristina M Furdui; S Bruce King
Journal:  Essays Biochem       Date:  2020-02-17       Impact factor: 8.000

Review 9.  Redox Signaling by Reactive Electrophiles and Oxidants.

Authors:  Saba Parvez; Marcus J C Long; Jesse R Poganik; Yimon Aye
Journal:  Chem Rev       Date:  2018-08-27       Impact factor: 60.622

10.  Reactivity, Selectivity, and Stability in Sulfenic Acid Detection: A Comparative Study of Nucleophilic and Electrophilic Probes.

Authors:  Vinayak Gupta; Hanumantharao Paritala; Kate S Carroll
Journal:  Bioconjug Chem       Date:  2016-05-09       Impact factor: 4.774
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