Synthesis of deuterated [D32]oleic acid and its phospholipid derivative [D64]dioleoyl-sn-glycero-3-phosphocholine
Synthesis of deuterated [D32]oleic acid and its phospholipid derivative [D64]dioleoyl-sn-glycero-3-phosphocholine
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DOI：
10.1002/jlcr.3088
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发表时间：
2013-07-01
影响因子：
1.8
通讯作者：
James, Michael
中科院分区：
文献类型：
--
作者：
Darwish, Tamim A.;Luks, Emily;James, Michael
油酸及其磷脂衍生物是细胞膜结构和功能的基础。因此，人们对它们的氘代形式的可用性越来越感兴趣，用于许多核磁共振、红外、质谱和中子散射研究。在这里，我们首次提出了一个简单的，大规模（克量）的高氘代[D-32]油酸的合成，通过使用多个，但简单，高产率的反应。用于合成[D-32]油酸的前体是[D-14]壬二酸和[D-17]壬酸，其通过使用金属催化的水热H/D交换反应将其H-1形式完全氘化（> 98%D）而获得。油酸是用Ca. 94% D同位素纯度，无反式异构体（反式油酸）污染。还描述了随后由[D-32]油酸合成[D-64]二油酰基-sn-甘油基-3-磷酸胆碱。版权所有（c）2013约翰威利父子有限公司
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 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. Copyright (c) 2013 John Wiley & Sons, Ltd.