Spiropyran as Building Block in Peptide Synthesis and Modulation of Photochromic Properties

Light-controlled triggering of materials requires efficient embedding of molecular photoswitches into larger molecules. We herein present the synthesis of two new building blocks for the synthesis of photoswitchable peptides, embedding spiropyranes as a central unit into peptide-backbones via a nove...

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Bibliographic Details
Published in:Organic letters 2024-12, Vol.26 (49), p.10542-10547
Main Authors: Paschold, André, Starke, Niclas, Rothemund, Sven, Binder, Wolfgang H.
Format: Article
Language:English
Subjects:
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Letter
Molecular Structure
Nitro Compounds - chemical synthesis
Nitro Compounds - chemistry
Peptides - chemical synthesis
Peptides - chemistry
Photochemical Processes
Solid-Phase Synthesis Techniques
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Summary:Light-controlled triggering of materials requires efficient embedding of molecular photoswitches into larger molecules. We herein present the synthesis of two new building blocks for the synthesis of photoswitchable peptides, embedding spiropyranes as a central unit into peptide-backbones via a novel, yet unreported approach. The synthesis presented here allows us to embed spiropyranes directly into solid-phase peptide synthesis (SPPS), further describing the resulting photophysical properties of the as-prepared photoswitchable peptides.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03929