Issue 23, 2020

Silanol: a bifunctional group for peptide synthesis and late-stage functionalization

Abstract

Chemical modification of a specific amino acid residue on peptides represents an efficient strategy to improve their pharmacokinetics and facilitates the potential to achieve post-synthetic diversification of peptides. Herein, we reported the first Pd-catalyzed late-stage ortho-olefination of Tyr residues on peptides with high chemo- and site-selectivity, by employing the easily attached and removable silanol as a bifunctional protecting group and directing group. Up to hexapeptides with variation on amino acid sequences or locations of the Tyr residue and different olefins were compatible with this protocol, which enriched the chemical toolbox for late-stage modification via C(sp2)–H functionalization. Furthermore, the orthogonal protection strategies of Tyr were also developed and could be applied to SPPS.

Graphical abstract: Silanol: a bifunctional group for peptide synthesis and late-stage functionalization

Supplementary files

Article information

Article type
Edge Article
Submitted
30 Apr 2020
Accepted
24 May 2020
First published
03 Jun 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 6070-6074

Silanol: a bifunctional group for peptide synthesis and late-stage functionalization

Q. Hu, K. Hou, J. Li, Y. Ge, Z. Song, A. S. C. Chan and X. Xiong, Chem. Sci., 2020, 11, 6070 DOI: 10.1039/D0SC02439B

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