Nucleophilic catalysis of hydrazone formation and transimination: implications for dynamic covalent chemistry

J Am Chem Soc. 2006 Dec 13;128(49):15602-3. doi: 10.1021/ja067189k.

Abstract

Aniline accelerates hydrazone formation and transimination through nucleophilic catalysis. To demonstrate the method, unprotected peptides are reacted and then scrambled using a hydrazone reaction under conditions relevant for biological applications. The strong enhancement in the rate of hydrazone equilibration broadens the scope of this stable imine in the field of dynamic covalent chemistry.

Publication types

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

MeSH terms

  • Aniline Compounds / chemistry*
  • Catalysis
  • Hydrazones / chemical synthesis*
  • Hydrazones / metabolism
  • Hydrogen-Ion Concentration
  • Hydrolysis
  • Kinetics
  • Temperature

Substances

  • Aniline Compounds
  • Hydrazones
  • aniline