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Synthesis 2009(24): 4256-4267  
DOI: 10.1055/s-0029-1217074
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Azobenzene-Based ω-Amino Acids and Related Building Blocks: Synthesis, Properties, and Application in Peptide Chemistry

Karola Rück-Braun*, Stefan Kempa, Beate Priewisch, Anja Richter, Sabine Seedorff, Lukas Wallach
Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 135, 10623 Berlin, Germany
Fax: +49(30)31428625; e-Mail: karola.rueck-braun@tu-berlin.de;
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Publication History

Received 13 July 2009
Publication Date:
22 October 2009 (online)

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Abstract

Azobenzenes are widely used as optical triggers for the development of photoresponsive materials. Starting from the literature-known ω-amino acids 4,4′-APB 1a and 4,4′-AMPB 2a, meta-substituted analogues were synthesized for the incorporation into peptides and proteins. While 4,4′-APB 1a requires special chemistry for peptide synthesis, an Fmoc/t-Bu protecting group strategy is applicable for 3,3′-APB 1b. The versatility of this and other novel azobenzene ω-amino acids is demonstrated by the preparation of cyclic photoswitchable phosphopeptides with the binding motif pTyr-Val-Asn-Val. Photochromic properties of the azo subunits and of the corresponding peptides are also presented.

Key words

azo compounds - amino acids - peptides - photoswitch - photochromism

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