Salicylaldehyde ester-induced chemoselective peptide ligations: enabling generation of natural peptidic linkages at the serine/threonine sites

Org Lett. 2010 Apr 16;12(8):1724-7. doi: 10.1021/ol1003109.

Abstract

A serine/threonine-based chemoselective ligation method is described. It uses an O-salicylaldehyde ester at the C-terminus, reacting with N-terminal serine or threonine to realize peptide ligations. The utility of the O-salicylaldehyde ester enables the rapid coupling reaction and the production of an N,O-benzylidene acetal intermediate, which is readily converted into natural peptidic linkages (Xaa-Ser/Thr) at the ligation site.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Peptides / chemistry*
  • Serine / chemistry*
  • Substrate Specificity
  • Threonine / chemistry*

Substances

  • Aldehydes
  • Peptides
  • salicylaldehyde
  • Threonine
  • Serine