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. 2009 Mar 17;106(11):4106-11.
doi: 10.1073/pnas.0809052106. Epub 2009 Feb 27.

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

Liang Zhao  1 , Oliver Baslé, Chao-Jun Li
Affiliations

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

Liang Zhao et al. Proc Natl Acad Sci U S A. .

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.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Fig. 1.
Fig. 1.
C-functionalization of N terminus of peptides.
Scheme 1.
Scheme 1.
Scheme 2.
Scheme 2.
Scheme 3.
Scheme 3.
Proposed mechanism for the arylation reaction.
Scheme 4.
Scheme 4.
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