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


ABSTRACT: 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.

SUBMITTER: Park CM 

PROVIDER: S-EPMC4782721 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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

Park Chung-Min CM   Johnson Brett A BA   Duan Jicheng J   Park Jeong-Jin JJ   Day Jacob J JJ   Gang David D   Qian Wei-Jun WJ   Xian Ming M  

Organic letters 20160212 5


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  ...[more]

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