Protein Modification of Lysine with 2-(2-Styrylcyclopropyl)ethanal

Org Lett. 2019 Dec 20;21(24):10043-10047. doi: 10.1021/acs.orglett.9b03982. Epub 2019 Dec 11.

Abstract

A new lysine-reactive cyclopropropyl aldehyde for the covalent modification of proteins was developed. The reagent exploits a divinylcyclopropane-cycloheptadiene rearrangement to render the initial condensation irreversible. A labeling study on eGFP demonstrated excellent chemoselectivity for the modification of amine-nucleophiles with the possibility of subsequent modifications.

MeSH terms

  • Green Fluorescent Proteins / chemistry*
  • Lysine / chemistry*
  • Molecular Structure
  • Styrenes / chemistry*

Substances

  • Styrenes
  • Green Fluorescent Proteins
  • Lysine