Synthesis of deuterated [D-32]oleic acid and its phospholipid derivative [D-64]dioleoyl-sn-glycero-3-phosphocholine

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dc.contributor.authorDarwish, TAen_AU
dc.contributor.authorLuks, Een_AU
dc.contributor.authorMoraes, Gen_AU
dc.contributor.authorYepuri, NRen_AU
dc.contributor.authorHolden, PJen_AU
dc.contributor.authorJames, Men_AU
dc.date.accessioned2014-07-17T01:52:40Zen_AU
dc.date.available2014-07-17T01:52:40Zen_AU
dc.date.issued2013-07-16en_AU
dc.date.statistics2014-07-16en_AU
dc.description.abstractOleic 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 [D32]oleic acid by using multiple, yet simple and high yielding reactions. The precursors for the synthesis of [D32]oleic acid are [D14]azelaic acid and [D17]nonanoic acid, which were obtained by complete deuteration (>98% D) of their 1H 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 [D64]dioleoyl-sn-glycero-3-phosphocholine from [D32]oleic acid is also described. Copyright © 2013 John Wiley & Sons, Ltd.© 2013, Wiley-Blackwell.en_AU
dc.identifier.citationDarwish, 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. Journal of Labelled Compounds and Radiopharmaceuticals, 56(9-10), 520-529. doi:10.1002/jlcr.3088en_AU
dc.identifier.govdoc5434en_AU
dc.identifier.issn0362-4803en_AU
dc.identifier.issue9-10en_AU
dc.identifier.journaltitleJournal of Labelled Compounds and Radiopharmaceuticalsen_AU
dc.identifier.pagination520-529en_AU
dc.identifier.urihttp://dx.doi.org/10.1002/jlcr.3088en_AU
dc.identifier.urihttp://apo.ansto.gov.au/dspace/handle/10238/5764en_AU
dc.identifier.volume56en_AU
dc.language.isoenen_AU
dc.publisherWiley-Blackwellen_AU
dc.subjectOleic aciden_AU
dc.subjectDeuterationen_AU
dc.subjectChemical reactionsen_AU
dc.subjectCarboxylic acidsen_AU
dc.subjectNonanoic aciden_AU
dc.titleSynthesis of deuterated [D-32]oleic acid and its phospholipid derivative [D-64]dioleoyl-sn-glycero-3-phosphocholineen_AU
dc.typeJournal Articleen_AU
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