Charting molecular composition of phosphatidylcholines by fatty acid scanning and ion trap MS3 fragmentation

Ekroos, Kim; Ejsing, Christer S.; Bahr, U.; Karas, Michael; Simons, Kai; Shevchenko, Andrej

doi:10.1194/jlr.d300020-jlr200

Cited by 292 publications

(344 citation statements)

References 45 publications

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“…2 -MS2). Similar fragmentation patterns to those observed in this study using -MS and -MS 2 have been already reported (Ekroos et al, 2003;Hsu and Turk, 2009). The recorded ion [M-CH3] -in -MS 2 was subjected to -MS 3 and four fragments groups were observed (Fig.…”

Section: Fragmentation In Negative Modesupporting

confidence: 73%

“…2-MS3). The patterns I, II and III have been reported elsewhere (Ekroos et al, 2003). In the present research, the decarboxylation of PUFAs (fragmentation pattern IV) of the six investigated PtdCho standards ( (Fig.…”

Section: IImentioning

confidence: 96%

“…In this kind of instrument, the ions are selected by their mass and categorized by differences in a magnetic field. Magnetic sector analyzers for phospholipid analysis include time of flight (TOF) (Schiller et al, 2004), ion trap , quadrupole (Han and Gross, 1994;Hsu and Turk, 2003), Fourier transform-ion ciclotron resonance (FT-ICR) (Yu et al, 2006), and hybrid instruments, for instance quadrupole-time of flight (QqTOF) (Ekroos et al, 2003), quadrupole ion trap (Garrett et al, 2011) and quadrupole ion trap-time of flight (QIT-TOF) (Hayasaka et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

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Plackett-Burman Design and Fragmentation Studies to Assist the Comparison of Techniques used to Extract Phospholipids Prior to Regiospecific Characterization by Liquid Chromatography Mass Spectrometry

Araujo¹,

Zhu²,

Breivik³

et al. 2016

AJMC

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A Plackett-Burman design was used for screening 12 variables that could affect the mass spectrometry signals of phosphatidylcholines (PtdCho) and proposing optimal fragmentation conditions to study the fragmentation mechanisms of PtdCho standards. Under optimal conditions, three well-established methods for extracting phospholipids from biological samples, specifically liquid-liquid extraction (LLE), normal phase liquid chromatography (NPLC) and high performance thin layer chromatography (HPTLC), were compared in terms of the number of regiospecifically characterized PtdCho by means of liquid chromatography three-stage mass spectrometry (LCMS 3 ). The same number of PtdCho species (35) were characterized by LCMS 3 in the LLE and NPLC fractions, whereas only 15 in the HPTLC fraction.

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Section: Fragmentation In Negative Modesupporting

confidence: 73%

Section: IImentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Plackett-Burman Design and Fragmentation Studies to Assist the Comparison of Techniques used to Extract Phospholipids Prior to Regiospecific Characterization by Liquid Chromatography Mass Spectrometry

Araujo¹,

Zhu²,

Breivik³

et al. 2016

AJMC

View full text Add to dashboard Cite

show abstract

“…Even comparisons to synthetic standards can be challenging due to the regioimpurity of some of these formulations arising from transacylation during preparation. Ekroos and co-workers undertook a careful analysis of the phosphatidylcholine regioisomers and compared negative ion CID data with the results of the phospholipase A2 assay, which employs an enzyme to selectively hydrolyze the fatty acyl substituent at sn-2 [33]. This study showed that with careful calibration, the relative proportions of the two sn-positional isomers could be established from CID ion abundances and importantly revealed that both synthetic and biologically derived lipids were present as mixtures of both regioisomers.…”

Section: Assigning Backbone Regiochemistrymentioning

confidence: 99%

Time to Face the Fats: What Can Mass Spectrometry Reveal about the Structure of Lipids and Their Interactions with Proteins?

Brown

Mitchell

Oakley

et al. 2012

J. Am. Soc. Mass Spectrom.

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Since the 1950s, X-ray crystallography has been the mainstay of structural biology, providing detailed atomic-level structures that continue to revolutionize our understanding of protein function. From recent advances in this discipline, a picture has emerged of intimate and specific interactions between lipids and proteins that has driven renewed interest in the structure of lipids themselves and raised intriguing questions as to the specificity and stoichiometry in lipid-protein complexes. Herein we demonstrate some of the limitations of crystallography in resolving critical structural features of ligated lipids and thus determining how these motifs impact protein binding. As a consequence, mass spectrometry must play an important and complementary role in unraveling the complexities of lipid-protein interactions. We evaluate recent advances and highlight ongoing challenges towards the twin goals of (1) complete structure elucidation of low, abundant, and structurally diverse lipids by mass spectrometry alone, and (2) assignment of stoichiometry and specificity of lipid interactions within protein complexes.Key words: Lipid-protein interactions, Structural biology, Structural lipidomics, Protein mass spectrometry Lipid-Protein Interactions P roteins and lipids, both integral for the function of all biological systems, are chemically distinct. A protein's three-dimensional structure and ultimately its function are defined by peptide-bonded amino acids and subsequent posttranslational modifications. In contrast, lipids are smaller molecules than proteins, but have a larger array of building blocks and linkage chemistries. Because of these inherent chemical differences, the optimal tools for de novo structural characterization differ between proteins and lipids.Lipid-protein interactions are critical for maintaining biological function in the membrane bilayer, the cytosol, and extracellular space. In the membrane, the chemical structures of lipid solvent molecules are important for the correct folding, insertion, structure, and function of membrane proteins. The interactions between enzymes and their respective lipid substrates are critical for correct substrate recognition and catalysis (e.g., lipoxygenase [1]). Additionally, lipid-protein interactions are increasingly being realized as important in maintaining cellular structure (e.g., cytoskeletal anchoring [2]), scaffolding and localization of multi-subunit protein complexes (e.g., associated kinase anchoring protein complexes [3]), and as second messengers in signal transduction (e.g., protein kinase C [4]).

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“…They also developed an analytical method and conducted stereochemistry studies of all the HDHAs produced by human platelets and rat brain homogenates using chiral LC-thermospray-MS and GC/MS (electron-impact ionization) [11]. Low-energy ionization primarily generates molecular (or pseudo-molecular) ions for collision-induced dissociation (CID) MS/MS analysis, through which the MS/MS spectra obtained are used widely to identify and elucidate the structures of lipid mediators derived from polyunsaturated fatty acids [12][13][14][15][16][17][18][19][20]. The lowenergy CID of eicosanoids includes charge-remote and charge-directed fragmentations [12,21], many of which occur through "␣-hydroxy-␤-ene like rearrangement" as referred to by Murphy, i.e., ␣-cleavage of the carbonOcarbon bond (␣ position to hydroxy group), facilitated by a double bond (ene) in the ␤ position [22].…”

mentioning

confidence: 99%

Resolvin D1, protectin D1, and related docosahexaenoic acid-derived products: Analysis via electrospray/low energy tandem mass spectrometry based on spectra and fragmentation mechanisms

Hong

Lü

Rong

et al. 2007

J. Am. Soc. Mass Spectrom.

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Resolvin D1 (RvD1) and protectin D1 (Neuroprotectin D1, PD1/NPD1) are newly identified anti-inflammatory lipid mediators biosynthesized from docosahexaenoic acid (DHA). In this report, the spectra-structure correlations and fragmentation mechanisms were studied using electrospray low-energy collision-induced dissociation tandem mass spectrometry (MS/MS) for biogenic RvD1 and PD1, as well as mono-hydroxy-DHA and related hydroperoxy-DHA. The loss of H 2 O and CO 2 in the spectra indicates the number of functional group(s). Chain-cut ions are the signature of the positions and numbers of functional groups and double bonds. The observed chain-cut ion is equivalent to a hypothetical homolytic-segment (cc, cm, mc, or mm) with addition or extraction of up to 2 protons (H). The ␣-cleavage ions are equivalent to: [cc ϩ H], with H from the hydroxyl through a ␤-ene or ␥-ene rearrangement; [cm Ϫ 2H], with 2H from hydroxyls of PD1 through a ␥-ene rearrangement, or 1H from the hydroxyl and the other H from the ␣-carbon of mono-HDHA through an ␣-H-␤-ene rearrangement; [mc Ϫ H], with H from hydroxyl through a ␤-ene or ␥-ene rearrangement, or from the ␣-carbon through an ␣-H-␤-ene rearrangement; or [mm] through charge-direct fragmentations. The ␤-ene or ␥-ene facilitates the H shift to ␥ position and ␣-cleavage. Deuterium labeling confirmed the assignment of MS/MS ions and the fragmentation mechanisms. Based on the MS/MS spectra and fragmentation mechanisms, we identified RvD1, PD1, and mono-hydroxy-DHA products in human neutrophils and blood, trout head-kidney, and stroke-injury murine braintissue. (J Am Soc Mass Spectrom 2007, 18, 128 -144)

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Charting molecular composition of phosphatidylcholines by fatty acid scanning and ion trap MS3 fragmentation

Cited by 292 publications

References 45 publications

Plackett-Burman Design and Fragmentation Studies to Assist the Comparison of Techniques used to Extract Phospholipids Prior to Regiospecific Characterization by Liquid Chromatography Mass Spectrometry

Plackett-Burman Design and Fragmentation Studies to Assist the Comparison of Techniques used to Extract Phospholipids Prior to Regiospecific Characterization by Liquid Chromatography Mass Spectrometry

Time to Face the Fats: What Can Mass Spectrometry Reveal about the Structure of Lipids and Their Interactions with Proteins?

Resolvin D1, protectin D1, and related docosahexaenoic acid-derived products: Analysis via electrospray/low energy tandem mass spectrometry based on spectra and fragmentation mechanisms

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