ArticleAnalytical chemistry2013
Identification and quantitation of fatty acid double bond positional isomers: a shotgun lipidomics approach using charge-switch derivatization.
Article in Analytical chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 56 papers.
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Who cites it
56 citing papers in PubMed, 112 citations in OpenAlex.
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- Making Ozonolysis Mass Spectrometry More Accessible: A Simple LC-OzESI-MS Workflow for Carbon-Carbon Double Bond Position Elucidation in Lipids and Natural Products.Journal of the American Society for Mass Spectrometry · 2026Article
- Structural Diversity and Analytical Characterization of Acylhomocarnitines.Journal of proteome research · 2026Article
- Dual fragmentation via collision-induced and oxygen attachment dissociations using water and its radicals for C=C position-resolved lipidomics.Communications chemistry · 2025Article
- Determination of double bond positions in unsaturated fatty acids by pre-column derivatization with dimethyl and dipyridyl disulfide followed by LC-SWATH-MS analysis.Analytical and bioanalytical chemistry · 2025Article
- Mapping Lipid C═C Isomer Profiles of Human Gut Bacteria through a Novel Structural Lipidomics Workflow Assisted by Chemical Epoxidation.Analytical chemistry · 2024Article
- Structural Elucidation and Relative Quantification of Fatty Acid Double Bond Positional Isomers in Biological Tissues Enabled by Gas-Phase Charge Inversion Ion/Ion Reactions.Analysis & sensing · 2024Article
- Charge inversion under plasma-nanodroplet reaction conditions excludes Fischer esterification for unsaturated fatty acids: a chemical approach for type II isobaric overlap.Chemical science · 2024Article
- Mass Spectrometry-based Single-Cell Lipidomics: Advancements, Challenges, and the Path Forward.Trends in analytical chemistry : TRAC · 2023Article
- Mass Spectrometry Detects Sphingolipid Metabolites for Discovery of New Strategy for Cancer Therapy from the Aspect of Programmed Cell Death.Metabolites · 2023Review
- Ozone-enabled fatty acid discovery reveals unexpected diversity in the human lipidome.Nature communications · 2023Article
- On-Tissue Chemical Derivatization for Comprehensive Mapping of Brain Carboxyl and Aldehyde Metabolites by MALDI-MS Imaging.Journal of the American Society for Mass Spectrometry · 2023Article
- Utilizing Skyline to analyze lipidomics data containing liquid chromatography, ion mobility spectrometry and mass spectrometry dimensions.Nature protocols · 2022Review
- Quantitative Analysis and Structural Elucidation of Fatty Acids by Isobaric Multiplex Labeling Reagents for Carbonyl-Containing Compound (SUGAR) Tags andAnalytical chemistry · 2022Article
- Simultaneous multiplexed quantification and C=C localization of fatty acids with LC-MS/MS using isobaric multiplex reagents for carbonyl-containing compound (SUGAR) tags and C=C epoxidation.Analytica chimica acta · 2022Article
- Enhancing the Signal-to-Noise of Diagnostic Fragment Ions of Unsaturated Glycerophospholipids via Precursor Exclusion Ultraviolet Photodissociation Mass Spectrometry (PEx-UVPD-MS).Analytical chemistry · 2022Article
- Reactive Thread Spray Mass Spectrometry for Localization of C═C Bonds in Free Fatty Acids: Applications for Obesity Diagnosis.Analytical chemistry · 2022Article
- Structural Characterization of Unusual Fatty Acid Methyl Esters with Double and Triple Bonds Using HPLC/APCI-MSMolecules (Basel, Switzerland) · 2021Article
- Relative Quantitation of Unsaturated Phosphatidylcholines Using 193 nm Ultraviolet Photodissociation Parallel Reaction Monitoring Mass Spectrometry.Journal of the American Chemical Society · 2021Article
- Mass Spectrometry-Based Shotgun Lipidomics Using Charge-Switch Derivatization for Analysis of Complex Long-Chain Fatty Acids.Methods in molecular biology (Clifton, N.J.) · 2021Article
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Authors and funding
3 authors at 1 institution in 1 country.
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Abstract
The specific locations of double bonds in mammalian lipids have profound effects on biological membrane structure, dynamics and lipid second messenger production. Herein, we describe a shotgun lipidomics approach that exploits charge-switch derivatization with N-(4-aminomethylphenyl) pyridinium (AMPP) and tandem mass spectrometry for identification and quantification of fatty acid double bond positional isomers. Through charge-switch derivatization of fatty acids followed by positive-ion mode ionization and fragmentation analysis, a marked increase in analytic sensitivity (low fmol/μL) and the identification of double bond positional isomers can be obtained. Specifically, the locations of proximal double bonds in AMPP-derivatized fatty acids are identified by diagnostic fragment ions resulting from the markedly reduced 1,4-hydrogen elimination from the proximal olefinic carbons. Additional fragmentation patterns resulting from allylic cleavages further substantiated the double bond position assignments. Moreover, quantification of fatty acid double bond positional isomers is achieved by the linear relationship of the normalized intensities of characteristic fragment ions vs the isomeric compositions of discrete fatty acid positional isomers. The application of this approach for the analysis of fatty acids in human serum demonstrated the existence of two double bond isomers of linolenic acid (i.e., Δ(6,9,12) 18:3, γ-linolenic acid (GLA), and Δ(9,12,15) 18:3, α-linolenic acid (ALA)). Remarkably, the isomeric ratio of GLA vs ALA esterified in neutral lipids was 3-fold higher than the ratio of their nonesterified moieties. Through this developed method, previously underestimated or unidentified alterations in fatty acid structural isomers can be determined facilitating the identification of novel biomarkers and maladaptive alterations in lipid metabolism during disease.
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