title: 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.
authors.affiliation: Department of Chemistry, Washington State University, Pullman, WA 99164, USA.
authors.forename: Tyler D
authors.initials: TD
authors.lastname: Biggs
authors.affiliation: Department of Chemistry, Washington State University, Pullman, WA 99164, USA.
authors.forename: Laksiri
authors.initials: L
authors.lastname: Weerasinghe
authors.affiliation: Department of Chemistry, Washington State University, Pullman, WA 99164, USA.
authors.forename: Chung-Min
authors.initials: CM
authors.lastname: Park
authors.affiliation: Department of Chemistry, Washington State University, Pullman, WA 99164, USA.
authors.forename: Ming
authors.initials: M
authors.lastname: Xian
keywords: Aldehyde; Conjugation; S-Nitrosothiols; Thioazaylide; Thioimine