title: Synthesis of deuterated [D32 ]oleic acid and its phospholipid derivative [D64 ]dioleoyl-sn-glycero-3-phosphocholine.
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 [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 (1) H 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.
authors.affiliation: National Deuteration Facility, Australian Nuclear Science and Technology Organisation (ANSTO), Locked Bag 2001 Kirrawee, DC NSW, 2232, Australia.
authors.forename: Tamim A
authors.initials: TA
authors.lastname: Darwish
authors.forename: Emily
authors.initials: E
authors.lastname: Luks
authors.forename: Greta
authors.initials: G
authors.lastname: Moraes
authors.forename: Nageshwar R
authors.initials: NR
authors.lastname: Yepuri
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Holden
authors.forename: Michael
authors.initials: M
authors.lastname: James
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003903:Deuterium / Q000737:chemistry*; D003998:Dicarboxylic Acids / Q000737:chemistry; D005227:Fatty Acids / Q000737:chemistry; D005997:Glycerylphosphorylcholine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008745:Methylation; D019301:Oleic Acid / Q000138:chemical synthesis* / Q000737:chemistry*; D010713:Phosphatidylcholines
chemical_list: D003998:Dicarboxylic Acids; D005227:Fatty Acids; D010713:Phosphatidylcholines; C062820:dimethyl azelate; D019301:Oleic Acid; D005997:Glycerylphosphorylcholine; C008776:pelargonic acid; D003903:Deuterium; C017251:1,2-oleoylphosphatidylcholine
keywords: [D14]azelaic acid; [D17]nonanoic acid; deuterated oleic acid; deuterated phospholipid; dioleoyl-sn-glycero-3-phosphocholine; olefinic proton