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

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

References

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