Journal
TETRAHEDRON
Volume 76, Issue 51, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.131198
Keywords
Alkene; Catalysis; Energy transfer; Isomerization; Peptide
Categories
Funding
- WWU Munster
- Verband der Chemischen Industrie (Kekule Fellowship)
- Alexander von Humboldt Foundation
- EPSRC
- GSK
- Verband der Chemischen Industrie (FCI Fellowship)
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A bio-inspired, photocatalytic E -> Z isomerization of cinnamides is reported using inexpensive (-)-riboflavin (vitamin B-2) under irradiation at lambda = 402 nm. This operationally simple transformation is compatible with a range of amide derivatives including -NR2, -NHSO2R and N(Boc)(2) (up to 99:1 Z:E). Selective energy transfer from the excited state photocatalyst to the starting E-isomer ensures that directionality is achieved: The analogous process with the Z-isomer is inefficient due to developing allylic strain causing chromophore deconjugation. This is supported by X-ray analysis and Stern-Volmer photo-quenching studies. Preliminary validation of the method in manipulating the conformation of a simple model Leu-enkephalin penta-peptide is disclosed via the incorporation of a cinnamamide-based amino acid. (C) 2020 Published by Elsevier Ltd.
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