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Abstract
A bio-inspired, photocatalytic E → Z isomerization of cinnamides is reported using inexpensive (−)-riboflavin (vitamin B2) under irradiation at λ = 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.
Original language | English |
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Article number | 131198 |
Number of pages | 8 |
Journal | Tetrahedron |
Volume | 76 |
Issue number | 51 |
Early online date | 4 May 2020 |
DOIs | |
Publication status | Published - 18 Dec 2020 |
Keywords
- Alkene
- catalysis
- Energy transfer
- Isomerization
- Peptide
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Dive into the research topics of 'Contra-thermodynamic E → Z isomerization of cinnamamides via selective energy transfer catalysis'. Together they form a unique fingerprint.Projects
- 1 Finished
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Industrial Case Account 2016 | Robertson, Jack
Burley, G., Zagnoni, M. & Robertson, J.
EPSRC (Engineering and Physical Sciences Research Council)
1/10/16 → 1/04/21
Project: Research Studentship Case - Internally allocated