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

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

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  • 1Department of Cell Biology, Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA.


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.

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