Synthesis of deuterated [D32]oleic acid and its phospholipid derivative [D64]dioleoyl-sn-glycero-3-phosphocholine

被引：29

作者：

Darwish, Tamim A. ^{[1
]}

Luks, Emily ^{[1
]}

Moraes, Greta ^{[1
]}

Yepuri, Nageshwar R. ^{[1
]}

Holden, Peter J. ^{[1
]}

James, Michael ^{[1
,2
,3
]}

机构：

[1] ANSTO, Natl Deuterat Facil, Kirrawee Dc, NSW 2232, Australia

[2] Univ New S Wales, Sch Chem, Kensington, NSW 2052, Australia

[3] Australian Synchrotron, Clayton, Vic 3168, Australia

来源：

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 2013年 / 56卷 / 9-10期

关键词：

deuterated oleic acid; dioleoyl-sn-glycero-3-phosphocholine; deuterated phospholipid; D-17]nonanoic acid; D-14]azelaic acid; olefinic proton; ANGLE NEUTRON-SCATTERING; OLEIC-ACID; SELECTIVE REDUCTIONS; BIOLOGICAL-MEMBRANES; CARBOXYLIC-ACIDS; FATTY-ACIDS; BILAYERS; ESTERS; LIPIDS; NMR;

D O I：

10.1002/jlcr.3088

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：520 / 529

页数：10

共 52 条

[21]

Gehring L, 1998, J LIPID RES, V39, P1118

[22]

GUNSTONE FD, 1967, CHEM PHYS LIPIDS, V1, P209

[23] Viewing the Bilayer Hydrocarbon Core Using Neutron Diffraction [J].

Han, Xue ;

Hristova, Kalina .

JOURNAL OF MEMBRANE BIOLOGY, 2009, 227 (03) :123-131

[24] Design, synthesis, and evaluation of an isotopic labeling strategy for studying fatty acid-protein binding by NMR [J].

Han, Yong ;

Alexander, Timothy E. ;

Tochtrop, Gregory P. .

MOLECULAR BIOSYSTEMS, 2008, 4 (06) :551-557

[25]

Heyningen V., 1938, J BIOL CHEM, V125, P495

[26] PREPARATION OF FULLY DEUTERATED FATTY-ACIDS BY SIMPLE METHOD [J].

HSIAO, CYY ;

OTTAWAY, CA ;

WETLAUFER, DB .

LIPIDS, 1974, 9 (11) :913-915

[27] Assessment of the aggregation state of integral membrane proteins in reconstituted phospholipid vesicles using small angle neutron scattering [J].

Hunt, JF ;

McCrea, PD ;

Zaccai, G ;

Engelman, DM .

JOURNAL OF MOLECULAR BIOLOGY, 1997, 273 (05) :1004-1019

[28] Synthesis of 11-thialinoleic acid and 14-thialinoleic acid, inhibitors of soybean and human lipoxygenases [J].

Jacquot, Cyril ;

McGinley, Chris M. ;

Plata, Erik ;

Holman, Theodore R. ;

van der Donk, Wilfred A. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (22) :4242-4252

[29] SYNTHESIS OF A PERDEUTERATED PHOSPHOLIPID - 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHOCHOLINE-D72 [J].

KINGSLEY, PB ;

FEIGENSON, GW .

CHEMISTRY AND PHYSICS OF LIPIDS, 1979, 24 (02) :135-147

[30]

Le Brun A. P., 2013, J CHEM BIOL IN PRESS, P1, DOI 10.1166/jcbi.2013.1005

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