Direct 11CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions
Name
nihms894252.pdf
Description
Accepted version
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779.91 KB
Format
Adobe PDF
Checksum (MD5)
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Author(s)
Zhao, Wenjun
Lee, Hong Geun
Buchwald, Stephen Leffler
Hooker, Jacob M.
Alternative Title
Direct [superscript 11]CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions
Date Issued
May 2017
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Zhao, Wenjun, et al., "Direct 11 CN-labeling of unprotected peptides via palladium-mediated sequential cross-coupling reactions." Journal of the American Chemical Society 139, 21 (2017): p. 7152-55 doi 10.1021/JACS.7B02761 ©2017 Author(s)
Version
Author's final manuscript
Abstract
A practical procedure for [superscript 11]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 [superscript 11]C cyanide by temporal separation of nucleophile addition.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/JACS.7B02761
