9-Fluorenylmethyl (Fm) Disulfides: Biomimetic Precursors for Persulfides

被引：72

作者：

Park, Chung-Min ^{[1
]}

Johnson, Brett A. ^{[1
]}

Duan, Jicheng ^{[2
]}

Park, Jeong-Jin ^{[3
]}

Day, Jacob J. ^{[1
]}

Gang, David ^{[3
]}

Qian, Wei-Jun ^{[2
]}

Xian, Ming ^{[1
]}

机构：

[1] Washington State Univ, Dept Chem, Pullman, WA 99164 USA

[2] Pacific NW Natl Lab, Div Biol Sci, Richland, WA 99352 USA

[3] Washington State Univ, Tissue Imaging & Prote Lab, Pullman, WA 99164 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 05期

关键词：

HYDROGEN-SULFIDE; S-SULFHYDRATION; CHEMISTRY; BIOLOGY; H2S; BIOCHEMISTRY; MOLECULE; STRESS; CARBON;

D O I：

10.1021/acs.orglett.5b03557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The development of a functional disulfide, FmSSPy-A (Fm = 9-fluorenylmethyl; Py = pyridinyl), is reported. It can effectively convert small molecule and protein thiols (-SH) to form -S-SFm adducts under mild conditions. This method allows for a H2S-free and biomimetic protocol to generate highly reactive persulfides (in their anionic forms). The high nucleophilicity of persulfides toward a number of thiol-blocking reagents is also demonstrated. The method holds promise for further understanding the chemical biology of persulfides and S-sulfhydration.

引用

页码：904 / 907

页数：4

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