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Chiral High Performance Liquid Chromatography of Oxo-Fatty Acids

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Encyclopedia of Lipidomics

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Introduction

Unsaturated fatty acids can be oxygenated via enzymatic or free radical-mediated reactions into numerous bioactive lipid mediators. The oxidation yields hydroperoxy, hydroxy, and epoxy fatty acids as well as prostaglandins and isoprostanes. The same unsaturated fatty acid may be oxidized in different positions of its acyl chain, leading to many different positional isomers, each of which can occur in two enantiomeric forms. Enzymatic oxidation usually yields enantiomers, while free radical oxidation results in the formation of racemates. Metabolic studies have shown that the biological activity of oxygenated fatty acids is specifically associated with only one of the enantiomeric forms. The availability of chiral stationary phases has recently permitted effective separation of enantiomeric oxo-lipid species even in underivatized form. Background reviews on early chiral resolution of oxo-fatty acids may be found elsewhere (Christie 2011).

Racemic Oxo-Fatty Acids

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Abbreviations

AA:

arachidonic acid

COX:

cyclooxygenase

CYP:

cytochrome P450

DiHETEs:

dihydroxyeicosatetraenoic acids

DiHETrEs:

dihydroxyeicosatrienoic acids

EDP:

epoxydocosapentaenoic acids

EETs:

epoxyeicosatrienoic acids

EETeTr:

epoxyeicosatetraenoic acid

entPGE2 :

enantiomeric PGE2

entPGD2 :

enantiomeric PGD2

EpFAs:

epoxy fatty acids

HETE:

hydroxyeicosatetraenoic acid

HPETE:

hydroperoxyeicosatetraenoic acid

HPODE:

hydroperoxyoctadecadienoic acid

LOX:

lipoxygenase

LTs:

leukotrienes

LTB4 :

leukotriene B4

LXs:

lipoxins

MEKC:

micellar electrokinetic chromatography

PD1:

protectin D1

PG:

prostaglandins

PGE2/D2 :

prostaglandin E2/D2

PGF2 :

prostaglandin F2

PKA:

protein kinase A

sEH:

soluble epoxide hydrolase

SFC:

supercritical fluid chromatography

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Authors and Affiliations

  1. Banting and Best Department of Medical Research, University of Toronto, 112 College St, M5G 1L6, Toronto, Ontario, Canada

    A. Kuksis

  2. Faculty of Fisheries Sciences, Hokkaido University, 3-1-1 Minato-cho, 041-8611, Hakodate, Hokkaido, Japan

    Y. Itabashi

  3. Department of Medicine, University of Toronto, Toronto, Ontario, Canada

    W. Pruzanski

Authors
  1. A. Kuksis
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  2. Y. Itabashi
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  3. W. Pruzanski
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Corresponding author

Correspondence to A. Kuksis .

Editor information

Editors and Affiliations

  1. Yong Loo Lin School of Medicine Centre for Life Sciences, Singapore, Singapore

    Markus R. Wenk

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Kuksis, A., Itabashi, Y., Pruzanski, W. (2016). Chiral High Performance Liquid Chromatography of Oxo-Fatty Acids. In: Wenk, M. (eds) Encyclopedia of Lipidomics. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-7864-1_118-1

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  • DOI: https://doi.org/10.1007/978-94-007-7864-1_118-1

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  • Online ISBN: 978-94-007-7864-1

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