Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

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

Direct 11CN-Labeling of Unprotected Peptides via Palladium-Mediated Sequential Cross-Coupling Reactions
Stephen L. Buchwald, Wenjun Zhao, Hong Geun Lee, Jacob M. Hooker
A practical procedure for 11CN-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 [11C]cyanide by temporal separation of nucleophile addition.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b02761

DOI: 10.1021/jacs.7b02761

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