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Please use this identifier to cite or link to this item: http://apo.ansto.gov.au/dspace/handle/10238/5684

Title: Synthesis of deuterated [D-32]oleic acid and its phospholipid derivative [D-64]dioleoyl-sn-glycero-3-phosphocholine
Authors: Darwish, T A
Luks, E
Moraes, G
Yepuri, N R
Holden, P J
James, M
Keywords: LIPIDS
NUCLEAR MAGNETIC RESONANCE
OLEIC ACID
CARBOXYLIC ACIDS
ESTERS
MEMBRANES
Issue Date: 1-Jul-2013
Publisher: WILEY BLACKWELL
Citation: Darwish, T. A., Luks, E., Moraes, G., Yepuri, N. R., Holden, P. J., & James, M. (2013). Synthesis of deuterated [D-32]oleic acid and its phospholipid derivative [D-64]dioleoyl-sn-glycero-3-phosphocholine [Special Issue]. Journal of Labelled Compounds & Radiopharmaceuticals, 56(9-10), 520-529.
Abstract: Oleic acid and its phospholipid derivatives are fundamental to the structure and function of cellular membranes. As a result, there has been increasing interest in the availability of their deuterated forms for many nuclear magnetic resonance, infrared, mass spectroscopy and neutron scattering studies. Here, we present for the first time a straightforward, large-scale (gram quantities) synthesis of highly deuterated [D-32]oleic acid by using multiple, yet simple and high yielding reactions. The precursors for the synthesis of [D-32]oleic acid are [D-14]azelaic acid and [D-17]nonanoic acid, which were obtained by complete deuteration (>98% D) of their H-1 forms by using metal catalysed hydrothermal H/D exchange reactions. The oleic acid was produced with ca. 94% D isotopic purity and with no contamination by the trans-isomer (elaidic acid). The subsequent synthesis of [D-64]dioleoyl-sn-glycero-3-phosphocholine from [D-32]oleic acid is also described. © 2013, Wiley-Blackwell.
URI: http://dx.doi.org/10.1002/jlcr.3088
http://apo.ansto.gov.au/dspace/handle/10238/5684
ISSN: 0362-4803
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