Celia de la Calle Arregui
Optimised conditions for the synthesis of 17O and 18O labelled cholesterol
de la Calle Arregui, Celia; Purdie, Jonathan A.; Haslam, Catherine A.; Law, Robert V.; Sanderson, John M.
Authors
Jonathan A. Purdie
Catherine A. Haslam
Robert V. Law
Dr John Sanderson j.m.sanderson@durham.ac.uk
Associate Professor
Abstract
Conditions are described for the preparation of cholesterol with 17O and 18O labels from i-cholesteryl methyl ether using minimal amounts of isotopically enriched water. Optimum yields employed trifluoromethanesulfonic acid as catalyst in 1,4-dioxane at room temperature with 5 equivalents of water. An isotopic enrichment >90% of that of the water used for the reaction could be attained. Tetrafluoroboric acid could also be used as catalyst, at the expense of a lower overall reaction yield. Byproducts from the reaction included dicholesteryl ether, methyl cholesteryl ether, compounds formed by ether hydrolysis, and olefins arising from elimination reactions. Reactions in tetrahydrofuran yielded significant amounts of cholesteryl ethers formed by reaction with alcohols arising from hydrolysis of the solvent.
Citation
de la Calle Arregui, C., Purdie, J. A., Haslam, C. A., Law, R. V., & Sanderson, J. M. (2015). Optimised conditions for the synthesis of 17O and 18O labelled cholesterol. Chemistry and Physics of Lipids, 195, 58-62. https://doi.org/10.1016/j.chemphyslip.2015.12.003
Journal Article Type | Article |
---|---|
Acceptance Date | Dec 17, 2015 |
Online Publication Date | Dec 24, 2015 |
Publication Date | Feb 1, 2015 |
Deposit Date | Dec 22, 2015 |
Publicly Available Date | Mar 28, 2024 |
Journal | Chemistry and Physics of Lipids |
Print ISSN | 0009-3084 |
Publisher | Elsevier |
Peer Reviewed | Peer Reviewed |
Volume | 195 |
Pages | 58-62 |
DOI | https://doi.org/10.1016/j.chemphyslip.2015.12.003 |
Keywords | Cholesterol, Synthesis, Oxygen isotope. |
Files
Published Journal Article
(502 Kb)
PDF
Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/
Copyright Statement
© 2016 The Authors. Published by Elsevier Ireland Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/)
You might also like
The association of lipids with amyloid fibrils
(2022)
Journal Article
Peptide Lipidation in Lysophospholipid Micelles and Lysophospholipid-Enriched Membranes
(2021)
Journal Article
17O NMR spectroscopy as a tool to study hydrogen bonding of cholesterol in lipid bilayers
(2020)
Journal Article
Downloadable Citations
About Durham Research Online (DRO)
Administrator e-mail: dro.admin@durham.ac.uk
This application uses the following open-source libraries:
SheetJS Community Edition
Apache License Version 2.0 (http://www.apache.org/licenses/)
PDF.js
Apache License Version 2.0 (http://www.apache.org/licenses/)
Font Awesome
SIL OFL 1.1 (http://scripts.sil.org/OFL)
MIT License (http://opensource.org/licenses/mit-license.html)
CC BY 3.0 ( http://creativecommons.org/licenses/by/3.0/)
Powered by Worktribe © 2024
Advanced Search