Effect of Alkynyl Group on Reactivity in Photoaffinity Labeling with 2-Thienyl-Substituted α-Ketoamide

Chemistry. 2022 Feb 19;28(11):e202103925. doi: 10.1002/chem.202103925. Epub 2022 Jan 31.

Abstract

Minimalist photo-reactive probes, which consist of a photo-reactive group and a tag for detection of target proteins, are useful tools in chemical biology. Although several diazirine-based and aryl azide-based minimalist probes are available, no keto-based minimalist probe has yet been reported. Here we describe minimalist probes based on a 2-thienyl-substituted α-ketoamide bearing an alkyne group on the thiophene ring. The 3-alkyne probe showed the highest photo-affinity labeling efficiency.

Keywords: alkynes; photo-affinity labeling; spin density; thiophenes; α-ketoamides.

MeSH terms

  • Affinity Labels
  • Alkynes
  • Azides*
  • Photoaffinity Labels* / metabolism
  • Proteins

Substances

  • Affinity Labels
  • Alkynes
  • Azides
  • Photoaffinity Labels
  • Proteins