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Site-specific C-functionalization of free-(NH) peptides and glycine derivatives via direct C-H bond functionalization.

ABSTRACT: 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.

SUBMITTER: Zhao L

PROVIDER: S-EPMC2649206 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

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Site-specific C-functionalization of free-(NH) peptides and glycine derivatives via direct C-H bond functionalization.

Zhao Liang L Baslé Oliver O Li Chao-Jun CJ

Proceedings of the National Academy of Sciences of the United States of America 20090227 11

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 easi ...[more]

PMID: 19251635

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