Journal
ORGANIC LETTERS
Volume 11, Issue 18, Pages 4172-4175Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol901731w
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Funding
- NIH [IR21AG031437-01]
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tert-Butyl nitrite was identified as a safe and chemoselective nitrating agent that provides preferentially mononitro derivatives of phenolic substrates in the presence of potentially competitive functional groups. On the basis of our control experiments, we propose that the reaction proceeds through the formation of O-nitrosyl intermediates prior to C-nitration via homolysis and oxidation. The reported nitration method is compatible with tyrosine-containing peptides on solid support in the synthesis of fluorogenic substrates for characterization of proteases.
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