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Phosphine Mediated Conjugation of S-Nitrosothiols and Aldehydes.

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.

SUBMITTER: Biggs TD

PROVIDER: S-EPMC4467916 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature

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Phosphine Mediated Conjugation of S-Nitrosothiols and Aldehydes.

Biggs Tyler D TD Weerasinghe Laksiri L Park Chung-Min CM Xian Ming M

Tetrahedron letters 20150501 21

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. ...[more]

PMID: 26089576

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