The Regioselective Synthesis of o-Nitrobenzyl DOPA Derivatives

Tobias Schneider; Joshua Martin; Patrick M. Durkin; Vladimir Kubyshkin; Nediljko Budisa

doi:10.1055/s-0036-1588766

Synthesis, Table of Contents

Synthesis 2017; 49(12): 2691-2699
DOI: 10.1055/s-0036-1588766

paper

The Regioselective Synthesis of o-Nitrobenzyl DOPA Derivatives

Authors

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

Abstract

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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.

Key words

amino acids - DOPA - photocaged - o-nitrobenzyl group - protection group

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References

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