Literature DB >> 27123991

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

Vinayak Gupta1, Hanumantharao Paritala1, Kate S Carroll1.   

Abstract

The comparative reaction efficiencies of currently used nucleophilic and electrophilic probes toward cysteine sulfenic acid have been thoroughly evaluated in two different settings-(i) a small molecule dipeptide based model and (ii) a recombinant protein model. We further evaluated the stability of corresponding thioether and sulfoxide adducts under reducing conditions which are commonly encountered during proteomic protocols and in cell analysis. Powered by the development of new cyclic and linear C-nucleophiles, the unsurpassed efficiency in the capture of sulfenic acid under competitive conditions is achieved and thus holds great promise as highly potent tools for activity-based sulfenome profiling.

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Year:  2016        PMID： 27123991      PMCID： PMC4886738          DOI： 10.1021/acs.bioconjchem.6b00181

Source DB:  PubMed          Journal:  Bioconjug Chem        ISSN： 1043-1802            Impact factor:   4.774


  57 in total

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Journal:  Chem Commun (Camb)       Date:  2011-07-08       Impact factor: 6.222

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Authors:  C Tony Liu; Stephen J Benkovic
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4.  Rational design of reversible and irreversible cysteine sulfenic acid-targeted linear C-nucleophiles.

Authors:  Vinayak Gupta; Kate S Carroll
Journal:  Chem Commun (Camb)       Date:  2016-02-25       Impact factor: 6.222

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Review 6.  Chemical 'omics' approaches for understanding protein cysteine oxidation in biology.

Authors:  Stephen E Leonard; Kate S Carroll
Journal:  Curr Opin Chem Biol       Date:  2010-12-03       Impact factor: 8.822

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8.  Facile synthesis and biological evaluation of a cell-permeable probe to detect redox-regulated proteins.

Authors:  Young Ho Seo; Kate S Carroll
Journal:  Bioorg Med Chem Lett       Date:  2008-11-24       Impact factor: 2.823

9.  Sulfenic acid formation in human serum albumin by hydrogen peroxide and peroxynitrite.

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4.  Endogenous, regulatory cysteine sulfenylation of ERK kinases in response to proliferative signals.

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Review 5.  Detection, identification, and quantification of oxidative protein modifications.

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7.  Diverse Redoxome Reactivity Profiles of Carbon Nucleophiles.

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8.  The role of sulfenic acids in cellular redox signaling: Reconciling chemical kinetics and molecular detection strategies.

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