Rentier Cédric, Fukumoto Kentarou, Taguchi Akihiro, Hayashi Yoshio
Department of Medicinal Chemistry, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
J Pept Sci. 2017 Jul;23(7-8):496-504. doi: 10.1002/psc.2964. Epub 2017 Jan 25.
The 3-nitro-2-pyridinesulfenyl chloride, commonly abbreviated as Npys-Cl, was among the first stable heterocyclic sulfenyl halides to be isolated. After its discovery, the Npys group was widely used as a protecting group for the amines, alcohols and thiols. Herein, we have reviewed some of the aspects of the Npys-Cl moiety, and its most promising recent uses are summarized, from the stability of the Npys protection of amines, hydroxyls and thiols and removal conditions for potential applications in peptide synthesis, to one of its most successful applications for the formation of mixed disulfides. Indeed, Npys protects thiols and acts as an activator for disulfide bond formation, thereby facilitating thiol/disulfide exchange to the corresponding disulfides. The selectivity and mild reaction conditions opened up a wide range of applications in chemical biology as well. Finally, some of the most recent developments regarding the synthesis and applications of solid-phase Npys derivatives are discussed. Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.
3-硝基-2-吡啶硫代氯，通常缩写为Npys-Cl，是最早被分离出来的稳定杂环硫代卤化物之一。自其被发现后，Npys基团被广泛用作胺、醇和硫醇的保护基团。在此，我们综述了Npys-Cl部分的一些方面，并总结了其近期最有前景的用途，从Npys对胺、羟基和硫醇的保护稳定性以及在肽合成潜在应用中的去除条件，到其形成混合二硫键的最成功应用之一。事实上，Npys保护硫醇并作为二硫键形成的活化剂，从而促进硫醇/二硫键交换生成相应的二硫键。其选择性和温和的反应条件也在化学生物学中开辟了广泛的应用。最后，讨论了关于固相Npys衍生物合成和应用的一些最新进展。版权所有© 2017欧洲肽学会和约翰·威利父子有限公司。
