Reactions of singlet oxygen with cholesterol: a computational study

Tsouri, AM and Robinson, D ORCID: https://orcid.org/0000-0003-2760-7163, 2022. Reactions of singlet oxygen with cholesterol: a computational study. Molecular Physics: e2139305. ISSN 0026-8976

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Abstract

Production and subsequent reactions of singlet oxygen are a major problem for the safe storage and transportation of foodstuffs. The reactions of singlet oxygen with cholesterol, a molecule commonly found in cells in vivo and also widely found in foodstuffs, are well known experimentally, with the products of these reactions commonly observed. However, a detailed understanding of the reaction mechanisms and transition states and intermediates involved are less well understood. In the current study, we have employed density functional theory to investigate the nature of the reaction pathways of singlet oxygenand cholesterol, determining the transition states and free energies of reaction. We have identified epoxide-like intermediates in the formation of 5-hydroperoxycholesterol and S-6-hydroperoxycholesterol which may be involved in the formation of 5,6-epoxide derivatives of cholesterol, which are an indicator of liver function. These results have given more detailed insight into the reaction of singlet oxygen with cholesterol.

Item Type:	Journal article
Publication Title:	Molecular Physics
Creators:	Tsouri, A.M. and Robinson, D.
Publisher:	Taylor & Francis
Date:	2 November 2022
ISSN:	0026-8976
Identifiers:	Number Type 10.1080/00268976.2022.2139305 DOI 1615298 Other
Rights:	This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial-NoDerivatives License (http://creativecommons. org/licenses/by-nc-nd/4.0/), which permits non-commercial re-use, distribution, and reproduction in any medium, provided the original work is properly cited, and is not altered, transformed, or built upon in any way.
Divisions:	Schools > School of Science and Technology
Record created by:	Jonathan Gallacher
Date Added:	09 Nov 2022 16:19
Last Modified:	09 Nov 2022 16:19
URI:	https://irep.ntu.ac.uk/id/eprint/47360

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