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• W2994893154 abstract "Lipids are important cellularbiomolecules that perform essential functional and biological roles. Forinstance, lipids in the cell are the compartmentalizer for the cytoplasm and anenergy storage unit. The knowledge surrounding lipids is abundant, yet there isstill so much to uncover. There are many categories of lipids and within eachcategory the structural composition is extremely diverse. In turn, the dramaticstructural complexity of lipids demands analytical methods capable of providingin-depth structural characterization of individual molecular structures. However,lipid structural elucidation has remained challenging, namely due to thepresence of isomeric and isobaric species with a complex mixture. Inparticular, isomeric/isobaric lipid structures arise from variations in class,headgroup, fatty acyl chain, sn-position,and/or carbon-carbon double bond (C=C) position(s). Recently, recent researchsuggests C=C composition impacts lipid physical properties, metabolic fate, andintermolecular interactions. Thus, analytical strategies capable of localizingsites of unsaturation are of interest in the lipidomics community.Mass spectrometry (MS) is aleading tool for lipid analysis. Electrospray ionization (ESI), a softionization method, is the most commonly used method for lipid ionization as ameans of taking the ions from liquid-phase to gas-phase without extensive decompositionof the species. Utilizing ESI-MS, lipids can be identified at a sumcompositional level via accurate mass measurements. . With tandem massspectrometers, lipid ions can be further probed, utilizing tandem-MS (MS/MS) togenerate structurally informative product ion spectra that facilitate theassignment of lipid molecular structure. More so, gas-phase ion/ion reactionsrepresent a unique MS-based technique that has improved the analysis of lipidsstructures. Gas-phase ion/ion reactions allow for lipid species to be chargeinverted from one polarity to the opposite polarity. This reaction enableslipids to be ionized in a polarity that is optimal for class identification andfurther investigated in the opposite polarity where more structural informationis obtained. All the information provided is captured without the requirementof multiple solution conditions which is necessary when analyzing in bothpolarities. In the case of charge inverted lipids from positive ion mode tonegative ion mode, fatty acyl composition can be obtained; however, C=Cinformation is lacking.MS can also be paired with otheranalytically technologies to assist with lipid analysis. One of thosetechnologies is liquid chromatography (LC), which allows for the separation oflipids based on different characteristic depending on the column type beingused. Reverse-phase LC (RPLC) allows for the separation of lipid molecularspecies based on structural composition. RPLC-MS/MS benefits from the abilityto separate lipids and determine their fatty acyl chain composition but it isdifficult to specify C=C location with the use of a synthetic standard that isidentical to each molecular species being analyzed.Commonality between thegas-phase ion/ion reactions for charge inversion of lipids and RPLC-MS/MSapproaches is the inability to provide C=C coverage. In-solution and unique ionactivation techniques have been developed for seeking such information. ThePaterno–Buchi reaction is a UV-initiated [2 + 2]-cycloaddition of an excited carbonylcontaining compound onto an olefin group. This reaction can be initiated ontothe alkene group within an unsaturated lipid aliphatic chain to form an oxetanering modification. There are two product ions that can be formed upon eachunsaturation site due to a lack of regioselectivity the reagent can attach ateither side of the C=C. The modified lipids can be taken into gas-phase andcollisionally activated via low-energy collision induced dissociation,generating product ions indictive of C=C position(s). The work herein shows theincorporation of the PB reaction into the gas-phases ion/ion reaction andRPLC-MS/MS apparatuses for C=C localization. The methods have been applied tothe lipid extracts of bovine liver and human plasma for confident moleculespecies determination." @default.
• W2994893154 created "2019-12-26" @default.
• W2994893154 creator A5072361407 @default.
• W2994893154 date "2019-12-10" @default.
• W2994893154 modified "2023-09-23" @default.
• W2994893154 title "Incorporation of the Paternò–Büchi reaction into mass spectrometry-based systems for lipid structural characterization" @default.
• W2994893154 doi "https://doi.org/10.25394/pgs.11327954.v1" @default.
• W2994893154 hasPublicationYear "2019" @default.
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