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Investigating isomer specific photoprotection in a model plant sunscreen

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Abstract

Sinapate esters are used throughout the plant kingdom, for example in photoprotection from ultraviolet radiation. Sinapate esters are naturally produced in their E-isomeric form; however, upon exposure to ultraviolet radiation, photoisomerization drives Z-isomer formation. To elucidate the photoprotection capacity of E vs. Z forms of sinapate esters, we explore the photochemistry of the model system, Z-ethyl sinapate. Following a novel Z-ethyl sinapate synthesis, we demonstrate that photoprotection is isomer independent. This suggests that, regarding photoprotection, there were no evolutionary pressures for biosynthesis of either isomer.

Graphical abstract: Investigating isomer specific photoprotection in a model plant sunscreen

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Publication details

The article was received on 24 Nov 2017, accepted on 29 Dec 2017 and first published on 02 Jan 2018


Article type: Communication
DOI: 10.1039/C7CC09061G
Citation: Chem. Commun., 2018, Advance Article
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    Investigating isomer specific photoprotection in a model plant sunscreen

    M. D. Horbury, A. L. Flourat, S. E. Greenough, F. Allais and V. G. Stavros, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C7CC09061G

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