Reassessment of Stereochemical Configuration of Natural Phosphatidylglycerols by Chiral-Phase High-Performance Liquid Chromatography and Electrospray Mass Spectrometry

Itabashi, Yutaka; Kuksis, A.

doi:10.1006/abio.1997.2418

Cited by 39 publications

(34 citation statements)

References 19 publications

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“…Electrospray ionization has been used to analyze molecular species of GPGro in animal and bacterial cells (Itabashi & Kuksis, 1997;Cabrera et al, 2000). Most of that research was performed by monitoring the molecular anions [M À H] À with tandem mass spectrometry to identify the fatty-acyl substituents esterified to the glycerol backbone.…”

Section: Glycerophosphoglycerol (Gpgro) Lipidsmentioning

confidence: 99%

Electrospray mass spectrometry of phospholipids

Pulfer

Murphy

2003

Mass Spectrometry Reviews

850

764

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Phospholipids play a central role in the biochemistry of all living cells. These molecules constitute the lipid bilayer defining the outer confines of a cell, but also serve as the structural entities which confine subcellular components. Mass spectrometry has emerged as a powerful tool useful for the qualitative and quantitative analysis of complex phospholipids, including glycerophospholipids and the sphingolipid, sphingomyelin. Collision induced decomposition of both positive and negative molecular ion species yield rich information as to the polar head group of the phospholipid and the fatty-acyl substituents esterified to the glycerophospholipid backbone. This review presents the current level of understanding of the mechanisms involved in the formation of various product ions following collisional activation of molecular ion species generated by electrospray ionization of the common glycerophospholipids, including phosphatidic acid, phosphatidylethanolamine, phosphatidylcholine, phosphatidylinositol, phosphatidylglycerol, phosphatidylserine, cardiolipin, and sphingomyelin. Recent advances in the application of matrix assisted laser desorption ionization is also considered. Several applications of mass spectrometry applied to phospholipid analysis are presented as they apply to physiology as well as pathophysiology.

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Section: Glycerophosphoglycerol (Gpgro) Lipidsmentioning

confidence: 99%

Electrospray mass spectrometry of phospholipids

Pulfer

Murphy

2003

Mass Spectrometry Reviews

850

764

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“…This latter property is of importance since cellular BMP is a mixture of different isomers having both fatty acyl location and glycerol configuration differences (14). Then, esterification of BMP isomers by naproxen leads to diastereoisomers which may be resolved more easily by chiral HPLC (33).…”

Section: Resultsmentioning

confidence: 99%

High-Performance Liquid Chromatography Determination of Bis(monoacylglycerol) Phosphate and Other Lysophospholipids

Luquain¹,

Laugier²,

Lagarde³

et al. 2001

Analytical Biochemistry

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“…The chiral-phase HPLC also revealed that some bacteria have a significant amount of a PG diastereomer (the R,R form; Fig. 2D), whose proportion increased gradually with increasing growth temperature, suggesting adaptation toward environmental change [19][20][21] .…”

Section: Separation Of Diastereomeric and Enantiomeric Glycerophosphomentioning

confidence: 99%

Chiral separation of glycerolipids by high-performance liquid chromatography

Itabashi

2012

Shishitsu Eiyogaku

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SummarySince the enantiomer resolution of synthetic mono-and diacylglycerols as 3,5-dinitrophenylurethanes was achieved by chiral-phase high-performance liquid chromatography (HPLC) in the 1980s, the methodology has been extended to the resolution of various synthetic and naturally occurring chiral glycerolipids. The recent development of polysaccharide-based chiral stationary phases along with optimized chromatographic elution conditions has permitted direct enantiomer resolution of mono-, di-, and triacylglycerols without previous derivatization. However, there are still some compounds for which enantiomer resolution is difficult to achieve, such as phosphatidylcholine and phosphatidylethanolamine. With the development of new derivatization reagents and chromatographic techniques, resolution of these difficult compounds may be possible in the near future. Chiral-phase HPLC will become considerably important in the future as a valuable tool for further expansion of the field of lipidomics and a better understanding of lipid metabolism.

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Reassessment of Stereochemical Configuration of Natural Phosphatidylglycerols by Chiral-Phase High-Performance Liquid Chromatography and Electrospray Mass Spectrometry

Cited by 39 publications

References 19 publications

Electrospray mass spectrometry of phospholipids

Electrospray mass spectrometry of phospholipids

High-Performance Liquid Chromatography Determination of Bis(monoacylglycerol) Phosphate and Other Lysophospholipids

Chiral separation of glycerolipids by high-performance liquid chromatography

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