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Synfacts 2019; 15(07): 0817
DOI: 10.1055/s-0039-1689776
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Photoredox-Catalyzed Decarboxylative Alkynylation of Peptides

Contributor(s):
Hisashi Yamamoto
,
An Wu
Garreau M, Le Vaillant F, Waser J. * Ecole Polytechnique Fédérale de Lausanne, Switzerland
C-Terminal Bioconjugation of Peptides through Photoredox Catalyzed Decarboxylative Alkynylation.

Angew. Chem. Int. Ed. 2019;
58: 8182-8186
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Further Information

Publication History

Publication Date:
17 June 2019 (online)

 
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Key words

photoredox catalysis - decarboxylation - alkynylation - C-terminal selectivity - hypervalent iodine reagents - metal-free

Significance

This paper provides a decarboxylative strategy for the alkynylation of the C-terminus of peptides, starting from free carboxylic acids. C-Terminal selectivity can be achieved in the presence of carboxylic acid side chains, and a broad range of functional groups are tolerated in the ­reaction system.


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Comment

The authors have developed a metal-free decarboxylative alkynylation of the C-terminus of peptides. The reaction proceeds rapidly and cleanly and might be useful for modifying peptides.


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