Literature DB >> 26089576

Phosphine Mediated Conjugation of S-Nitrosothiols and Aldehydes.

Tyler D Biggs1, Laksiri Weerasinghe1, Chung-Min Park1, Ming Xian1.   

Abstract

S-Nitrosothiols (SNO) and their biological implications as an important post-translational modification are under active investigation. In our work on bioorthogonal reactions of protein SNO we have uncovered chemistry of this functionality that shows synthetic promise. Herein we report a phosphine-mediated reaction between SNO and aldehydes to form thioimines. A simple synthesis of benzoisothiazole based on this reaction is presented.

Entities:  

Keywords:  Aldehyde; Conjugation; S-Nitrosothiols; Thioazaylide; Thioimine

Year:  2015        PMID： 26089576      PMCID： PMC4467916          DOI： 10.1016/j.tetlet.2015.04.017

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  14 in total

Review 1.  Nitric oxide donors: chemical activities and biological applications.

Authors:  Peng George Wang; Ming Xian; Xiaoping Tang; Xuejun Wu; Zhong Wen; Tingwei Cai; Adam J Janczuk
Journal:  Chem Rev       Date:  2002-04       Impact factor: 60.622

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.  Signaling by S-nitrosylation in the heart.

Authors:  Elizabeth Murphy; Mark Kohr; Sara Menazza; Tiffany Nguyen; Alicia Evangelista; Junhui Sun; Charles Steenbergen
Journal:  J Mol Cell Cardiol       Date:  2014-01-16       Impact factor: 5.000

4.  Antimicrobial activity of some 1,2-benzisothiazoles having a benzenesulfonamide moiety.

Authors:  F Zani; P Vicini
Journal:  Arch Pharm (Weinheim)       Date:  1998-06       Impact factor: 3.751

5.  Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases.

Authors:  Paola Vicini; Athina Geronikaki; Matteo Incerti; Bernadetta Busonera; Graziella Poni; Carla Alba Cabras; Paolo La Colla
Journal:  Bioorg Med Chem       Date:  2003-11-03       Impact factor: 3.641

6.  2-Thiazolylimino/heteroarylimino-5-arylidene-4-thiazolidinones as new agents with SHP-2 inhibitory action.

Authors:  A Geronikaki; P Eleftheriou; P Vicini; I Alam; A Dixit; A K Saxena
Journal:  J Med Chem       Date:  2008-08-15       Impact factor: 7.446

Review 7.  Proteomic approaches to evaluate protein S-nitrosylation in disease.

Authors:  Laura M López-Sánchez; Chary López-Pedrera; Antonio Rodríguez-Ariza
Journal:  Mass Spectrom Rev       Date:  2013-06-15       Impact factor: 10.946

Review 8.  Protein cysteine thiol nitrosation: maker or marker of reactive nitrogen species-induced nonerythroid cellular signaling?

Authors:  Jack R Lancaster
Journal:  Nitric Oxide       Date:  2008-05-06       Impact factor: 4.427

9.  Exploration of the "traceless" reductive ligation of S-nitrosothiols.

Authors:  Jiming Zhang; Hua Wang; Ming Xian
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

Review 10.  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
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  2 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

2.  Automated Online Solid-Phase Derivatization for Sensitive Quantification of Endogenous S-Nitrosoglutathione and Rapid Capture of Other Low-Molecular-Mass S-Nitrosothiols.

Authors:  Xin Wang; Carlos T Garcia; Guanyu Gong; John S Wishnok; Steven R Tannenbaum
Journal:  Anal Chem       Date:  2018-01-09       Impact factor: 6.986
  2 in total

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