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Synthesis of deuterated [D 32 ]oleic acid and its phospholipid derivative [D 64 ]dioleoyl‐ sn ‐glycero‐3‐phosphocholine
Author(s) -
Darwish Tamim A.,
Luks Emily,
Moraes Greta,
Yepuri Nageshwar R.,
Holden Peter J.,
James Michael
Publication year - 2013
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3088
Subject(s) - chemistry , oleic acid , azelaic acid , elaidic acid , deuterium , phosphocholine , phospholipid , infrared spectroscopy , organic chemistry , nuclear chemistry , membrane , fatty acid , biochemistry , physics , quantum mechanics , phosphatidylcholine , linoleic acid
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 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 [D 64 ]dioleoyl‐ sn ‐glycero‐3‐phosphocholine from [D 32 ]oleic acid is also described. Copyright © 2013 John Wiley & Sons, Ltd.