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dc.contributor.authorDarwish, TA-
dc.contributor.authorLuks, E-
dc.contributor.authorMoraes, G-
dc.contributor.authorYepuri, NR-
dc.contributor.authorHolden, PJ-
dc.contributor.authorJames, M-
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 [Special Issue]. Journal of Labelled Compounds & Radiopharmaceuticals, 56(9-10), 520-529.en_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 [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.en_AU
dc.publisherWILEY BLACKWELLen_AU
dc.subjectOleic Aciden_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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