Literature DB >> 21080645

One-pot thioether formation from S-nitrosothiols.

Dehui Zhang1, Nelmi O Devarie-Baez, Jia Pan, Hua Wang, Ming Xian.   

Abstract

Protein S-nitrosation is an important post-translational modification. However, the detection of S-nitrosation is still problematic because S-nitrosation products, that is, S-nitrosothiols, are unstable species. Here a new reaction which can selectively convert unstable S-nitrosothiols to stable thioethers in one-pot under very mild conditions is reported. This reaction has the potential to be applied in the detection of protein S-nitrosation.

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Year:  2010        PMID： 21080645      PMCID： PMC3074955          DOI： 10.1021/ol102491n

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


  18 in total

1.  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 2.  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 3.  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

4.  Detection and characterization of protein nitrosothiols.

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

Review 5.  S-Nitrosothiol measurements in biological systems.

Authors:  Andrew Gow; Allan Doctor; Joan Mannick; Benjamin Gaston
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2007-02-25       Impact factor: 3.205

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

Authors:  Jiming Zhang; Sheng Li; Dehui Zhang; Hua Wang; A Richard Whorton; Ming Xian
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

Review 7.  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

8.  Allylic disulfide rearrangement and desulfurization: mild, electrophile-free thioether formation from thiols.

Authors:  David Crich; Franck Brebion; Venkataramanan Krishnamurthy
Journal:  Org Lett       Date:  2006-08-03       Impact factor: 6.005

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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  10 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

2.  A reductive ligation based fluorescent probe for S-nitrosothiols.

Authors:  Di Zhang; Wei Chen; Zhengrui Miao; Yong Ye; Yufen Zhao; S Bruce King; Ming Xian
Journal:  Chem Commun (Camb)       Date:  2014-05-14       Impact factor: 6.222

3.  Protecting group-free glycoligation by the desulfurative rearrangement of allylic disulfides as a means of assembly of oligosaccharide mimetics.

Authors:  Venkataraman Subramanian; Myriame Moumé-Pymbock; Tianshun Hu; David Crich
Journal:  J Org Chem       Date:  2011-03-23       Impact factor: 4.354

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

5.  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

6.  Identification of protein nitrosothiols using phosphine-mediated selective reduction.

Authors:  Sheng Li; Hua Wang; Ming Xian; A Richard Whorton
Journal:  Nitric Oxide       Date:  2011-11-10       Impact factor: 4.427

7.  Rapid and selective nitroxyl (HNO) trapping by phosphines: kinetics and new aqueous ligations for HNO detection and quantitation.

Authors:  Julie A Reisz; Charles N Zink; S Bruce King
Journal:  J Am Chem Soc       Date:  2011-07-11       Impact factor: 15.419

Review 8.  Direct methods for detection of protein S-nitrosylation.

Authors:  Nelmi O Devarie-Baez; Dehui Zhang; Sheng Li; A Richard Whorton; Ming Xian
Journal:  Methods       Date:  2013-04-29       Impact factor: 3.608

9.  Selective trapping of SNO-BSA and GSNO by benzenesulfinic acid sodium salt: mechanistic study of thiosulphonate formation and feasibility as a protein S-nitrosothiol detection strategy.

Authors:  Benjamin D Reeves; Jonathan K Hilmer; Lisa Mellmann; Myra Hartzheim; Kevin Poffenberger; Keith Johnson; Neelambari Joshi; David J Singel; Paul A Grieco
Journal:  Tetrahedron Lett       Date:  2013-10-16       Impact factor: 2.415

10.  A clickable probe for versatile characterization of S-nitrosothiols.

Authors:  Jenna L Clements; Franziska Pohl; Pandi Muthupandi; Stephen C Rogers; Jack Mao; Allan Doctor; Vladimir B Birman; Jason M Held
Journal:  Redox Biol       Date:  2020-09-01       Impact factor: 11.799
  10 in total

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