Synthesis 2017; 49(12): 2691-2699
DOI: 10.1055/s-0036-1588766
paper
© Georg Thieme Verlag Stuttgart · New York

The Regioselective Synthesis of o-Nitrobenzyl DOPA Derivatives

Tobias Schneider
Institute of Chemistry, Technical University of Berlin, Müller-Breslau-Str. 10, 10623 Berlin, Germany   Email: nediljko.budisa@tu-berlin.de
,
Joshua Martin
Institute of Chemistry, Technical University of Berlin, Müller-Breslau-Str. 10, 10623 Berlin, Germany   Email: nediljko.budisa@tu-berlin.de
,
Patrick M. Durkin
Institute of Chemistry, Technical University of Berlin, Müller-Breslau-Str. 10, 10623 Berlin, Germany   Email: nediljko.budisa@tu-berlin.de
,
Vladimir Kubyshkin
Institute of Chemistry, Technical University of Berlin, Müller-Breslau-Str. 10, 10623 Berlin, Germany   Email: nediljko.budisa@tu-berlin.de
,
Nediljko Budisa*
Institute of Chemistry, Technical University of Berlin, Müller-Breslau-Str. 10, 10623 Berlin, Germany   Email: nediljko.budisa@tu-berlin.de
› Author Affiliations
Further Information

Publication History

Received: 03 March 2017

Accepted after revision: 06 March 2017

Publication Date:
13 April 2017 (eFirst)

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.

Supporting Information

 
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