Cyclic Acyl Disulfides and Acyl Selenylsulfides as the Precursors for Persulfides (RSSH), Selenylsulfides (RSeSH), and Hydrogen Sulfide (H2S),Organic Letters

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Cyclic Acyl Disulfides and Acyl Selenylsulfides as the Precursors for Persulfides (RSSH), Selenylsulfides (RSeSH), and Hydrogen Sulfide (H2S)
Organic Letters ( IF 4.9 ) Pub Date : 2018-01-18 00:00:00 , DOI: 10.1021/acs.orglett.7b04005
Jianming Kang ₁ , Aaron J Ferrell ₁ , Wei Chen ₁ , Difei Wang ₂ , Ming Xian ₁

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The reactions of three model compounds (1–3) for cyclic acyl disulfides and cyclic acyl selenylsulfides are studied. These compounds were found to be effective precursors for persulfides (RSSH) and selenylsulfides (RSeSH) upon reacting with nucleophilic species. They could also act as H₂S donors when interacting with cellular thiols. The most interesting discovery was the generation of RSeSH from compound 3 under mild conditions. Selenylsulfides (RSeSH) are expected to be important regulating molecules involved in Sec-related redox signaling. The method of producing RSeSH should allow researchers to better understand the chemical biology of RSeSH.

中文翻译：

环状酰基二硫化物和酰基硒基硫化物作为过硫化物 (RSSH)、硒基硫化物 (RSeSH) 和硫化氢 (H2S) 的前体

研究了环状酰基二硫醚和环状酰基硒基硫醚的三种模型化合物( 1-3 )的反应。人们发现这些化合物在与亲核物质反应时是过硫化物 (RSSH) 和硒基硫化物 (RSeSH) 的有效前体。当与细胞硫醇相互作用时，它们还可以充当 H ₂ S 供体。最有趣的发现是在温和条件下从化合物3生成 RSeSH 。硒基硫化物 (RSeSH) 有望成为参与 Sec 相关氧化还原信号传导的重要调节分子。产生 RSeSH 的方法应该可以让研究人员更好地了解 RSeSH 的化学生物学。

更新日期：2018-01-18

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