Site-Selective Modification of α-Amino Acids and Oligopeptides via Native Amine-Directed γ-C(sp3)-H Arylation

Org Lett. 2019 Dec 6;21(23):9381-9385. doi: 10.1021/acs.orglett.9b03607. Epub 2019 Nov 18.

Abstract

Site-selective modification of chemically and biologically valuable α-amino acids and peptides is of great importance for biochemical study and pharmaceutical development. Few methods based on remote C(sp3)-H functionalization of aliphatic side-chains of peptides has been disclosed in recent years. In this report, we developed a novel approach for γ-C(sp3)-H and γ-/δ-C(sp2)-H arylation of α-amino acids with α-hydrogen by native amine-directed C-H functionalization and further realized the γ-C(sp3)-H arylation of N-terminally unprotected peptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Amino Acids / chemistry*
  • Carbon / chemistry
  • Oligopeptides / chemistry*
  • Silver / chemistry

Substances

  • Amines
  • Amino Acids
  • Oligopeptides
  • Silver
  • Carbon