ω-Di-(trideuteromethyl)-tocotrienols as probes for membrane orientation and dynamics of tocotrienols
Publication type: Journal Article
Publication date: 2008-11-01
scimago Q3
wos Q4
SJR: 0.271
CiteScore: 2.0
Impact factor: 0.9
ISSN: 03624803, 10991344
Organic Chemistry
Drug Discovery
Biochemistry
Spectroscopy
Analytical Chemistry
Radiology, Nuclear Medicine and imaging
Abstract
The study of the dynamic and structural role of lipids in membranes is commonly accomplished using 2H NMR and neutron diffraction. This necessarily requires the availability of specifically deuterated lipids. Our interest in the behaviour of tocopherols and tocotrienols in phospholipid membranes has shown that the tocotrienols, unsaturated forms of vitamin E, have very different effects on membrane properties as judged by differential scanning calorimetry (DSC). We report here the preparation of deuterated forms of α-, β-, and γ-tocotrienols where the terminal methyl groups on the isoprenoid side chains have been replaced with trideuteromethyl groups, thus incorporating six deuterium atoms per molecule. Starting from the naturally occurring tocotrienols, the terminal alkene can be selectively hydrobrominated with NBS, transformed to a diol and oxidatively cleaved to give a chain truncated aldehyde. The full chain length is then restored by reaction with the ylide formed by deprotonation of triphenyl-(1,2,2,2-tetradeutero-1-trideuteromethyl-ethyl)-phosphonium bromide. Copyright © 2008 John Wiley & Sons, Ltd.
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West R., Wang Y., Atkinson J. ω-Di-(trideuteromethyl)-tocotrienols as probes for membrane orientation and dynamics of tocotrienols // Journal of Labelled Compounds and Radiopharmaceuticals. 2008. Vol. 51. No. 13. pp. 413-418.
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West R., Wang Y., Atkinson J. ω-Di-(trideuteromethyl)-tocotrienols as probes for membrane orientation and dynamics of tocotrienols // Journal of Labelled Compounds and Radiopharmaceuticals. 2008. Vol. 51. No. 13. pp. 413-418.
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TY - JOUR
DO - 10.1002/jlcr.1554
UR - https://doi.org/10.1002/jlcr.1554
TI - ω-Di-(trideuteromethyl)-tocotrienols as probes for membrane orientation and dynamics of tocotrienols
T2 - Journal of Labelled Compounds and Radiopharmaceuticals
AU - West, Ryan
AU - Wang, Yongsheng
AU - Atkinson, Jeffrey
PY - 2008
DA - 2008/11/01
PB - Wiley
SP - 413-418
IS - 13
VL - 51
SN - 0362-4803
SN - 1099-1344
ER -
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BibTex (up to 50 authors)
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@article{2008_West,
author = {Ryan West and Yongsheng Wang and Jeffrey Atkinson},
title = {ω-Di-(trideuteromethyl)-tocotrienols as probes for membrane orientation and dynamics of tocotrienols},
journal = {Journal of Labelled Compounds and Radiopharmaceuticals},
year = {2008},
volume = {51},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/jlcr.1554},
number = {13},
pages = {413--418},
doi = {10.1002/jlcr.1554}
}
Cite this
MLA
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West, Ryan, et al. “ω-Di-(trideuteromethyl)-tocotrienols as probes for membrane orientation and dynamics of tocotrienols.” Journal of Labelled Compounds and Radiopharmaceuticals, vol. 51, no. 13, Nov. 2008, pp. 413-418. https://doi.org/10.1002/jlcr.1554.