Development of an Intein-Inspired Amide Cleavage Chemical Device

J Org Chem. 2016 Jan 15;81(2):699-707. doi: 10.1021/acs.joc.5b02399. Epub 2015 Dec 28.

Abstract

A photoresponsive amide cleavage device was developed based on the asparagine imidation-mediated cleavage of peptide bonds during intein-mediated protein splicing. The chemical environment of the protein splicing process was mimicked by the incorporation of geminal dimethyl groups and a secondary amine unit in asparagine scaffold. Furthermore, the resulting photoresponsive device could induce the phototriggered cleavage of an amide bond by the protection of the secondary amine unit with an o-nitrobenzyloxycarbonyl group.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Amides / metabolism
  • Asparagine / chemistry*
  • Inteins / genetics*
  • Models, Molecular
  • Photochemical Processes
  • Protein Splicing

Substances

  • Amides
  • Asparagine