Functionalization of protected tyrosine via Sonogashira reaction: synthesis of 3-(1,2,3-triazolyl)-tyrosine

Mol Divers. 2016 May;20(2):469-81. doi: 10.1007/s11030-015-9642-y. Epub 2015 Oct 26.

Abstract

1,2,3-Triazol tyrosines were synthesized from tyrosine alkynes that were in turn prepared via Sonogashira cross-coupling reaction. The tyrosine alkynes were subjected to click-chemistry reaction conditions leading to the corresponding 3-(1,2,3-triazolyl)-tyrosines in yields ranging from moderate to good.

Keywords: Alkyne; Click chemistry; Peptide bond; Triazole; Tyrosine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Catalysis
  • Click Chemistry
  • Triazoles / chemistry*
  • Tyrosine / chemical synthesis*
  • Tyrosine / chemistry*

Substances

  • Alkynes
  • Triazoles
  • Tyrosine