Quinonemethide in Chemical Biology

Quinonemethides (QM) are reactive chemical species which can be generated from o- and p-hydroxy benzyl alcohol derivatives even in aqueous media. Its unique reactivity is frequently utilized in organic synthesis and chemical biology. The high electrophilicity of QM would result in the rapid formation of a covalent bond with nucleophilic amino-acid residues in peptide or nucleic-acid bases. In addition, released leaving groups in the formation of QM can be designed as, for example, bioactive molecules for drug-delivery system and fluorophores for activity-based probe. Herein, recent reports associated with the quinonemethide chemistry are described.