X-ray structure analysis of the cholesterol 25- and 20-hydroperoxides, the elusive primary sidechain autoxidation products of cholesterol

• Published in: Steroids Vol. 187; p. 109092
• Main Authors: Ali, Hasrat, van Lier, Johan E.
• Format: Journal Article
• Language: English
• Published: Elsevier Inc 01.11.2022
• Subjects: 25-hydroxycholesterol; Cholesterol; Cholesterol 20β(S)-hydroperoxide; Cholesterol 25-hydroperoxide; Hirshfeld surface analysis; X-ray analysis; Cholesterol 20β(S)-hydroperoxide; Ch25OH; Ch; FP; HS; Cholesterol; Cholesterol 25-hydroperoxide; 25-hydroxycholesterol; CH25H; Hirshfeld surface analysis; 2D; Ch25OOH; Ch20OOH; X-ray analysis
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/j.steroids.2022.109092

[Display omitted] •The X-ray structure analysis of the primary cholesterol sidechain autoxidation products, cholesterol 25- and 20-hydroperoxides, are presented and analyzed.•Comparison of torsional and bond angles of the sidechain carbons reveal characteristic differences between the conformation of the compounds.•Intermolecular interactions are visualized through Hirshfeld surface analyses and fingerprint plots.•Energy frameworks to calculate intermolecular interaction energies are presented. The systematic X-ray structure analyses of the primary cholesterol sidechain autoxidation products cholesterol 25- and 20β(S)-hydroperoxide are presented and compared to cholesterol and 25-hydroxycholesterol. Intermolecular interactions in crystal structures of the molecules are revealed through Hirshfeld surface analysis and fingerprint plots. The magnitude of energy frameworks is presented by combining efficient calculations of intermolecular interaction energies with novel graphical representation.