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Synfacts 2019; 15(06): 0685
DOI: 10.1055/s-0037-1612531
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Site-Selective γ-C(sp3)–H Silylation of Peptides

Contributor(s):
Hisashi Yamamoto
,
Sachin Suresh Bhojgude
Zhan B.-B, Fan J, Jin L, Shi B.-F. * Zhejiang University, Hangzhou, P. R. of China
Divergent Synthesis of Silicon-Containing Peptides via Pd-Catalyzed Post-Assembly γ-C(sp3)–H Silylation.

ACS Catal. 2019;
9: 3298-3303
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Further Information

Publication History

Publication Date:
20 May 2019 (online)

 
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Key words

late-stage functionalization - peptide modification - silylation - palladium catalysis - C–H activation

Significance

Chemically modified unnatural peptides are often endowed with improved biological and pharmacokinetic properties and are therefore valuable in the drug-discovery process. Modification by silicon-containing groups appears to be promising, because the presence of a silicon moiety in amino acids or peptides can help to improve permeation through membranes and increase proteolytic stability.


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Comment

Shi and co-workers have developed an efficient procedure for the synthesis of various γ-silyl-α-amino acids and oligopeptides by palladium(II)-catalyzed γ-C(sp3)–H silylation. The present site-specific late-stage C(sp3)–H functionalization is assisted by a picolinamide auxiliary and uses cheap and commercially available hexamethyldisilane as a silylating agent. Compatibility with a broad range of amino acid residues and the facile removal of the picolinamide auxiliary are noteworthy features of the present protocol.


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