Direct 11 CN-Labeling of Unprotected Peptides via Palladium-Mediated Sequential Cross-Coupling Reactions

A practical procedure for CN-labeling of unprotected peptides has been developed. The method was shown to be highly chemoselective for cysteine over other potentially nucleophilic residues, and the radiolabeled products were synthesized and purified in less than 15 min. Appropriate for biomedical ap...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-05, Vol.139 (21), p.7152-7155
Main Authors: Zhao, Wenjun, Lee, Hong Geun, Buchwald, Stephen L, Hooker, Jacob M
Format: Article
Language:English
Subjects:
Chemistry
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Summary:A practical procedure for CN-labeling of unprotected peptides has been developed. The method was shown to be highly chemoselective for cysteine over other potentially nucleophilic residues, and the radiolabeled products were synthesized and purified in less than 15 min. Appropriate for biomedical applications, the method could be used on an extremely small scale (20 nmol) with a high radiochemical yield. The success of the protocol stems from the use of a Pd-reagent based on a dihaloarene, which enables direct "nucleophile-nucleophile" coupling of the peptide and [ C]cyanide by temporal separation of nucleophile addition.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b02761