The Regioselective Synthesis of o-Nitrobenzyl DOPA Derivatives

Abstract

Photocaged DOPA derivatives may serve for non-invasive unmasking of the catechol fragment in biological systems. This would enable efficient control of the redox and metal-coordinating properties associated with the free catechol moiety, in particular, in biosynthetically produced adhesive proteins and synthetic peptides. Synthetic routes towards photocaged DOPA derivatives are reported herein. A new method for preparing para-alkylated DOPA starting from 3,4-dihydroxybenzaldehyde is described for the first time.