Fast and catalyst-free hydrazone ligation via ortho-halo-substituted benzaldehydes for protein C-terminal labeling at neutral pH?

Chemical Communications Pub Date: 2015-07-09 DOI: 10.1039/C5CC04382D

Abstract

Rapid and catalyst-free hydrazone ligation reaction between ortho-halobenzaldehyde derivatives and peptide/protein hydrazides was observed at neutral pH and room temperature. 2-Chlorobenzaldehyde exhibited the fastest reaction and highest conversion rates among the series of ortho-halobenzaldehydes. The resulting hydrazone-containing bioconjugation products were also found to be fairly stable under experimental conditions. The new ligation strategy was successfully used for protein C-terminal labeling and should provide a practical approach for the modification of proteins.

Graphical abstract: Fast and catalyst-free hydrazone ligation via ortho-halo-substituted benzaldehydes for protein C-terminal labeling at neutral pH
Recommended Literature