Synthesis of perdeuterated linoleic acid-d31 and chain deuterated 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine-d62

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dc.contributor.authorMoir, Men_AU
dc.contributor.authorYepuri, NRen_AU
dc.contributor.authorMarshall, DLen_AU
dc.contributor.authorBlanksby, SJen_AU
dc.contributor.authorDarwish, TAen_AU
dc.date.accessioned2023-09-18T05:48:03Zeu_AU
dc.date.available2023-09-18T05:48:03Zen_AU
dc.date.issued2022-08-08en_AU
dc.date.statistics2023-07-03en_AU
dc.description.abstractHerein, we report a gram-scale synthesis of perdeuterated linoleic acid-d31. The starting materials for the synthesis are two saturated fatty acids, azelaic acid-d14 and pentanoic acid-d9, which can be obtained by metal catalysed hydrothermal hydrogen-deuterium exchange. The synthesis utilises the fatty acids directly via decarboxylative coupling. Copper catalysed coupling of a terminal alkyne intermediate with a propargyl bromide derivative affords a skipped diyne, which can be reduced using P-2 nickel to obtain the desired cis,cis-diene geometry. The subsequent synthesis of the tail-deuterated phospholipid, 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine-d62 (PLPC-d62) is also described. Optimised reaction conditions were developed to access this phospholipid and its regioisomeric purity was characterised by two complementary mass spectrometry techniques. © 2022 The Authors - CC- BY Licenceen_AU
dc.description.sponsorshipThe National Deuteration Facility is partly supported by the National Collaborative Research Infrastructure Strategy an initiative of the Australian Government. The assistance of Dr Agata Rekas in preparing the deuterated fatty acid precursors for this work is gratefully acknowledged. Open access publishing facilitated by Australian Nuclear Science and Technology Organisation, as part of the Wiley – Australian Nuclear Science and Technology Organisation agreement via the Council of Australian University Librarians. The mass spectrometry-based regioisomer assays data reported in this paper were obtained at the QUT Central Analytical Research Facility.en_AU
dc.identifier.citationMoir, M., Yepuri, N. R., Marshall, D. L., Blanksby, S. J., & Darwish, T. A. (2022). Synthesis of perdeuterated linoleic acid-d31 and chain deuterated 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine-d62. Advanced Synthesis & Catalysis, 364(21), 3670-3681. doi:10.1002/adsc.202200616en_AU
dc.identifier.issn1615-4150en_AU
dc.identifier.issue21en_AU
dc.identifier.journaltitleAdvanced Synthesis & Catalysisen_AU
dc.identifier.pagination3670-3681en_AU
dc.identifier.urihttps://apo.ansto.gov.au/handle/10238/15120en_AU
dc.identifier.volume364en_AU
dc.language.isoenen_AU
dc.publisherJohn Wiley & Sonsen_AU
dc.relation.urihttps://doi.org/10.1002/adsc.202200616en_AU
dc.subjectDeuterationen_AU
dc.subjectLinoleic aciden_AU
dc.subjectSynthesisen_AU
dc.subjectPhospholipidsen_AU
dc.subjectMass spectroscopyen_AU
dc.subjectCell membranesen_AU
dc.subjectEnzymesen_AU
dc.subjectLipidsen_AU
dc.subjectDeuteriumen_AU
dc.subjectLabellingen_AU
dc.titleSynthesis of perdeuterated linoleic acid-d31 and chain deuterated 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine-d62en_AU
dc.typeJournal Articleen_AU
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