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Download fileDivergent Synthesis of Silicon-Containing Peptides via Pd-Catalyzed Post-Assembly γ‑C(sp3)–H Silylation
journal contribution
posted on 2019-03-12, 00:00 authored by Bei-Bei Zhan, Jun Fan, Liang Jin, Bing-Feng ShiSilicon-containing
peptides hold great promise for maintaining
or enhancing biological activity, while simultaneously improving the
proteolytic stability. Herein, we report the Pd(II)-catalyzed γ-C(sp3)–H silylation of α-amino acids and peptides.
Quinone-type ligands play a pivotal role in this reaction, and hexamethyldisilane
was used as silylation reagent. The facile removal of a picolinamide
auxiliary and the compatibility with a wide range of oligopeptides
bearing various α-amino acid residues render this protocol a
valuable strategy to access γ-silyl-α-amino acids and
peptides. This reaction enriches the chemical toolbox for the site-specific
peptide modification and showcases the vast potential of postsynthetic
diversification of peptides via late-stage C(sp3)–H
functionalization.