Literature DB >> 22644884

Chemoselective ligation of sulfinic acids with aryl-nitroso compounds.

Mauro Lo Conte1, Kate S Carroll.   

Abstract

Making a comeback: The inefficient condensation of sulfinic acid and aryl nitroso compounds has been transformed into a chemoselective process that converts sulfinic acid into stable cyclic sulfonamide analogues (see scheme). This ligation proceeds rapidly under aqueous conditions in high yield, and lays the groundwork for the development of sulfinic acid detection methods in biological systems.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22644884      PMCID: PMC3523331          DOI: 10.1002/anie.201201812

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  17 in total

1.  Quantitation of protein sulfinic and sulfonic acid, irreversibly oxidized protein cysteine sites in cellular proteins.

Authors:  Michael Hamann; Tiequan Zhang; Suzanne Hendrich; James A Thomas
Journal:  Methods Enzymol       Date:  2002       Impact factor: 1.600

2.  Reversible oxidation of the active site cysteine of peroxiredoxins to cysteine sulfinic acid. Immunoblot detection with antibodies specific for the hyperoxidized cysteine-containing sequence.

Authors:  Hyun Ae Woo; Sang Won Kang; Hyung Ki Kim; Kap-Seok Yang; Ho Zoon Chae; Sue Goo Rhee
Journal:  J Biol Chem       Date:  2003-10-14       Impact factor: 5.157

Review 3.  Expanding the functional diversity of proteins through cysteine oxidation.

Authors:  Khalilah G Reddie; Kate S Carroll
Journal:  Curr Opin Chem Biol       Date:  2008-09-17       Impact factor: 8.822

4.  Peroxide-dependent sulfenylation of the EGFR catalytic site enhances kinase activity.

Authors:  Candice E Paulsen; Thu H Truong; Francisco J Garcia; Arne Homann; Vinayak Gupta; Stephen E Leonard; Kate S Carroll
Journal:  Nat Chem Biol       Date:  2011-12-11       Impact factor: 15.040

Review 5.  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

Review 6.  Reduction of cysteine sulfinic acid in eukaryotic, typical 2-Cys peroxiredoxins by sulfiredoxin.

Authors:  W Todd Lowther; Alexina C Haynes
Journal:  Antioxid Redox Signal       Date:  2010-12-17       Impact factor: 8.401

Review 7.  The sulfinic acid switch in proteins.

Authors:  Claus Jacob; Andrea L Holme; Fiona H Fry
Journal:  Org Biomol Chem       Date:  2004-06-29       Impact factor: 3.876

8.  Colorimetric assay for methanesulfinic acid in biological samples.

Authors:  C F Babbs; M J Gale
Journal:  Anal Biochem       Date:  1987-05-15       Impact factor: 3.365

9.  ATP-dependent reduction of cysteine-sulphinic acid by S. cerevisiae sulphiredoxin.

Authors:  Benoît Biteau; Jean Labarre; Michel B Toledano
Journal:  Nature       Date:  2003-10-30       Impact factor: 49.962

10.  Interior surface modification of bacteriophage MS2.

Authors:  Jacob M Hooker; Ernest W Kovacs; Matthew B Francis
Journal:  J Am Chem Soc       Date:  2004-03-31       Impact factor: 15.419

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  27 in total

1.  Harnessing Redox Cross-Reactivity To Profile Distinct Cysteine Modifications.

Authors:  Jaimeen D Majmudar; Aaron M Konopko; Kristin J Labby; Christopher T M B Tom; John E Crellin; Ashesh Prakash; Brent R Martin
Journal:  J Am Chem Soc       Date:  2016-02-05       Impact factor: 15.419

Review 2.  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

3.  A Chemical Approach for the Detection of Protein Sulfinylation.

Authors:  Mauro Lo Conte; Jiusheng Lin; Mark A Wilson; Kate S Carroll
Journal:  ACS Chem Biol       Date:  2015-06-17       Impact factor: 5.100

Review 4.  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

Review 5.  Chemical Probes for Redox Signaling and Oxidative Stress.

Authors:  Masahiro Abo; Eranthie Weerapana
Journal:  Antioxid Redox Signal       Date:  2017-12-22       Impact factor: 8.401

Review 6.  The Expanding Landscape of the Thiol Redox Proteome.

Authors:  Jing Yang; Kate S Carroll; Daniel C Liebler
Journal:  Mol Cell Proteomics       Date:  2015-10-30       Impact factor: 5.911

Review 7.  Proteomic approaches to quantify cysteine reversible modifications in aging and neurodegenerative diseases.

Authors:  Liqing Gu; Renã A S Robinson
Journal:  Proteomics Clin Appl       Date:  2016-11-11       Impact factor: 3.494

Review 8.  Cysteine oxidative posttranslational modifications: emerging regulation in the cardiovascular system.

Authors:  Heaseung S Chung; Sheng-Bing Wang; Vidya Venkatraman; Christopher I Murray; Jennifer E Van Eyk
Journal:  Circ Res       Date:  2013-01-18       Impact factor: 17.367

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.  Chasing cysteine oxidative modifications: proteomic tools for characterizing cysteine redox status.

Authors:  Christopher I Murray; Jennifer E Van Eyk
Journal:  Circ Cardiovasc Genet       Date:  2012-10-01
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