Late Stage Phosphotyrosine Mimetic Functionalization of Peptides Employing Metallaphotoredox Catalysis

Org Lett. 2021 Jun 4;23(11):4244-4249. doi: 10.1021/acs.orglett.1c01200. Epub 2021 May 24.

Abstract

Access to phosphotyrosine (pTyr) mimetics requires multistep syntheses, and therefore late stage incorporation of these mimetics into peptides is not feasible. Here, we develop and employ metallaphotoredox catalysis using 4-halogenated phenylalanine to afford a variety of protected pTyr mimetics in one step. This methodology was shown to be tolerant of common protecting groups and applicable to the late stage pTyr mimetic modification of protected and unprotected peptides, and peptides of biological relevance.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Molecular Structure
  • Peptides / chemistry
  • Peptides / metabolism*
  • Phenylalanine / chemistry*
  • Phosphotyrosine / chemistry
  • Phosphotyrosine / metabolism*
  • Signal Transduction / physiology

Substances

  • Peptides
  • Phosphotyrosine
  • Phenylalanine