Literature DB >> 20731371

Reductive ligation mediated one-step disulfide formation of S-nitrosothiols.

Jiming Zhang1, Sheng Li, Dehui Zhang, Hua Wang, A Richard Whorton, Ming Xian.   

Abstract

A one-step reductive ligation mediated disulfide formation of S-nitrosothiols was developed. This reaction involves the reaction of the S-nitroso group with phosphine-thioesters to form sulfenamide and thiolate intermediates, which then undergo a fast intermolecular disulfide formation to form stable conjugates. This reaction can be used to design new biosensors of S-nitrosated proteins.

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Year:  2010        PMID: 20731371      PMCID: PMC2943486          DOI: 10.1021/ol101863s

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


  20 in total

1.  Mechanistic investigation of the staudinger ligation.

Authors:  Fiona L Lin; Helen M Hoyt; Herman van Halbeek; Robert G Bergman; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2005-03-02       Impact factor: 15.419

2.  Methodological vexation about thiol oxidation versus S-nitrosation -- a commentary on "An ascorbate-dependent artifact that interferes with the interpretation of the biotin-switch assay".

Authors:  Mark T Gladwin; Xunde Wang; Neil Hogg
Journal:  Free Radic Biol Med       Date:  2006-06-03       Impact factor: 7.376

Review 3.  Measurement of circulating nitrite and S-nitrosothiols by reductive chemiluminescence.

Authors:  Peter H MacArthur; Sruti Shiva; Mark T Gladwin
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2007-01-05       Impact factor: 3.205

Review 4.  Proteomic methods for analysis of S-nitrosation.

Authors:  Nicholas J Kettenhofen; Katarzyna A Broniowska; Agnes Keszler; Yanhong Zhang; Neil Hogg
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2007-02-25       Impact factor: 3.205

5.  Detection and characterization of protein nitrosothiols.

Authors:  Samie R Jaffrey
Journal:  Methods Enzymol       Date:  2005       Impact factor: 1.600

Review 6.  Detection of S-nitrosothiols in biological fluids: a comparison among the most widely applied methodologies.

Authors:  Daniela Giustarini; Aldo Milzani; Isabella Dalle-Donne; Ranieri Rossi
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2006-10-10       Impact factor: 3.205

Review 7.  Protein S-nitrosylation: purview and parameters.

Authors:  Douglas T Hess; Akio Matsumoto; Sung-Oog Kim; Harvey E Marshall; Jonathan S Stamler
Journal:  Nat Rev Mol Cell Biol       Date:  2005-02       Impact factor: 94.444

8.  Cell surface engineering by a modified Staudinger reaction.

Authors:  E Saxon; C R Bertozzi
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

Review 9.  S-Nitrosothiols: cellular formation and transport.

Authors:  Yanhong Zhang; Neil Hogg
Journal:  Free Radic Biol Med       Date:  2005-04-01       Impact factor: 7.376

Review 10.  S-nitrosylation in health and disease.

Authors:  Matthew W Foster; Timothy J McMahon; Jonathan S Stamler
Journal:  Trends Mol Med       Date:  2003-04       Impact factor: 11.951

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  25 in total

1.  Facile amide formation via S-nitrosothioacids.

Authors:  Jia Pan; Nelmi O Devarie-Baez; Ming Xian
Journal:  Org Lett       Date:  2011-01-27       Impact factor: 6.005

Review 2.  Chemical methods to detect S-nitrosation.

Authors:  Hua Wang; Ming Xian
Journal:  Curr Opin Chem Biol       Date:  2010-10-29       Impact factor: 8.822

Review 3.  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 4.  Strategies and tools to explore protein S-nitrosylation.

Authors:  Karthik Raju; Paschalis-Thomas Doulias; Margarita Tenopoulou; Jennifer L Greene; Harry Ischiropoulos
Journal:  Biochim Biophys Acta       Date:  2011-05-30

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

Review 7.  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

8.  Conversion of S-phenylsulfonylcysteine residues to mixed disulfides at pH 4.0: utility in protein thiol blocking and in protein-S-nitrosothiol detection.

Authors:  B D Reeves; N Joshi; G C Campanello; J K Hilmer; L Chetia; J A Vance; J N Reinschmidt; C G Miller; D P Giedroc; E A Dratz; D J Singel; P A Grieco
Journal:  Org Biomol Chem       Date:  2014-07-02       Impact factor: 3.876

Review 9.  Solid-phase capture for the detection and relative quantification of S-nitrosoproteins by mass spectrometry.

Authors:  J Will Thompson; Michael T Forrester; M Arthur Moseley; Matthew W Foster
Journal:  Methods       Date:  2012-10-11       Impact factor: 3.608

Review 10.  Oxidative stress and the HIV-infected brain proteome.

Authors:  Lerna Uzasci; Avindra Nath; Robert Cotter
Journal:  J Neuroimmune Pharmacol       Date:  2013-03-09       Impact factor: 4.147

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