Journal
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
Volume 106, Issue 11, Pages 4106-4111Publisher
NATL ACAD SCIENCES
DOI: 10.1073/pnas.0809052106
Keywords
amino acid; C-C bond formation; peptide modification
Categories
Funding
- Canada Research Chair (Tier I) Foundation
- Canada Foundation for Innovation
- Natural Sciences and Engineering Research Council (Canada)
- McGill University
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A copper-catalyzed alpha-functionalization of glycine derivatives and short peptides with nucleophiles is described. The present method provides ways to introduce functionalities such as aryl, vinyl, alkynyl, or indolyl specifically to the terminal glycine moieties of small peptides, which are normally difficult in peptide modifications. Furthermore, on functionalization, the configurations of other stereocenters in the peptides could be maintained. Because the functionalized peptides could easily be deprotected and carried onto the next coupling process, our approach provides a useful tool for the peptide-based biological research.
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