Aryl azide photochemistry in defined protein environments

Org Lett. 2013 Feb 15;15(4):728-31. doi: 10.1021/ol3028779. Epub 2013 Jan 25.

Abstract

A genetically encoded precursor to an aryl nitrene, para-azidophenylalanine, was introduced site specifically into proteins to deduce if distinct environments were capable of caging a reactive organic intermediate. Following photolysis of mutant T4 lysozyme or green fluorescent proteins, EPR spectra showed, respectively, the presence of a triplet nitrene and an anilino radical.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Bacteriophage T4 / enzymology
  • Bacteriophage T4 / genetics
  • Electron Spin Resonance Spectroscopy
  • Green Fluorescent Proteins / chemistry
  • Imines / chemistry
  • Molecular Structure
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemistry
  • Photochemistry
  • Photolysis
  • Ultraviolet Rays
  • Viral Proteins / chemistry
  • Viral Proteins / genetics

Substances

  • Azides
  • Imines
  • Viral Proteins
  • gene 5 protein, Enterobacteria phage T4
  • Green Fluorescent Proteins
  • phenylnitrene
  • 4-azidophenylalanine
  • Phenylalanine