Browsing by Author "Blanksby, SJ"
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- ItemSynthesis of perdeuterated linoleic acid-d31 and chain deuterated 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine-d62(John Wiley & Sons, 2022-08-08) Moir, M; Yepuri, NR; Marshall, DL; Blanksby, SJ; Darwish, TAHerein, 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 Licence