Journal
ORGANIC LETTERS
Volume 18, Issue 5, Pages 904-907Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03557
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Funding
- NIH [R01HL116571, P41 GM103493]
- DOE [DE-AC05-76RL01830]
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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.
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