Nucleophilic catalysis of hydrazone formation and transimination: implications for dynamic covalent chemistry.
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.
Dirksen
Anouk
A
Department of Cell Biology, Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA.
Dirksen
Sjoerd
S
Hackeng
Tilman M
TM
Dawson
Philip E
PE
D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D006835:Hydrazones / Q000138:chemical synthesis* / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007700:Kinetics; D013696:Temperature
D000814:Aniline Compounds; D006835:Hydrazones; C023650:aniline