Selective incorporation of nitrile-based infrared probes into proteins via cysteine alkylation

Biochemistry. 2010 Dec 14;49(49):10354-6. doi: 10.1021/bi101711a. Epub 2010 Nov 17.

Abstract

The nitrile stretching vibration is increasingly used as a sensitive infrared probe of local protein environments. However, site-specific incorporation of a nitrile moiety into proteins is difficult. Here we show that various aromatic nitriles can be easily incorporated into peptides and proteins via either thiol alkylation or arylation reaction.

Publication types

  • Comparative Study
  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkylation
  • Calmodulin / chemistry*
  • Calmodulin / metabolism
  • Cysteine / chemistry*
  • Cysteine / metabolism
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / metabolism
  • Humans
  • Nitriles / chemistry*
  • Nitriles / metabolism
  • Proteins / chemistry
  • Proteins / metabolism
  • Spectrophotometry, Infrared / methods
  • Vibration

Substances

  • CALML3 protein, human
  • Calmodulin
  • Fluorescent Dyes
  • Nitriles
  • Proteins
  • Cysteine