{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T03:13:25Z","timestamp":1791429205750,"version":"4.3.3"},"reference-count":56,"publisher":"American Chemical Society (ACS)","issue":"19","license":[{"start":{"date-parts":[[2020,8,25]],"date-time":"2020-08-25T00:00:00Z","timestamp":1598313600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2020,8,25]],"date-time":"2020-08-25T00:00:00Z","timestamp":1598313600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2020,8,25]],"date-time":"2020-08-25T00:00:00Z","timestamp":1598313600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21722506"],"award-info":[{"award-number":["21722506"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,10,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The Paterno\u0300\u2013Bu\u0308chi (PB) reaction is a photochemical reaction involving [2 + 2] cycloaddition between electronically excited carbonyl and carbon\u2013carbon double bond (C\ue5fbC). It has been established as a lipid derivatization strategy, leading to confident assignment of C\ue5fbC locations in lipids when coupled with tandem mass spectrometry (MS\/MS). Although acetone and several aryl-containing ketones or aldehydes have been explored as PB reagents, the chemical properties critical to achieving efficient conversion and minimum side reactions remain unclear. Herein, we investigated a set of acetophenone (AP) derivatives, aiming to provide insights into the development of new PB reagents with enhanced performance for lipid analysis. For AP derivatives, we found that electron-withdrawing groups (e.g., \u2212F and \u2212CF3) on the benzene ring improved the overall conversion, while a bulky group at the ortho-position decreased the conversion. Norrish Type I cleavage was largely diminished; however, the Norrish Type II side reaction was more competitive, producing products isomeric to the PB reaction products. Among all AP derivatives tested, 2\u2032,4\u2032,6\u2032-trifluoroacetophenone (triFAP) showed the best performance. It offered a relatively high PB yield (20\u201330%) for different types of C\ue5fbC, high sensitivity (sub-nM) for C\ue5fbC identification, and accurate isomer quantitation. Due to the significantly reduced chemical interferences in shotgun analysis, triFAP provided better performance than that from acetone PB-MS\/MS. An offline triFAP PB reaction was implemented in a liquid chromatography analysis workflow, which enabled the large-scale identification of phospholipids including C\ue5fbC location isomers from a complex lipid extract.<\/jats:p>","DOI":"10.1021\/acs.analchem.0c02896","type":"journal-article","created":{"date-parts":[[2020,8,25]],"date-time":"2020-08-25T10:38:18Z","timestamp":1598351898000},"page":"13470-13477","source":"Crossref","is-referenced-by-count":80,"title":["Next-Generation Paterno\u0300\u2013Bu\u0308chi\nReagents for Lipid Analysis by Mass Spectrometry"],"prefix":"10.1021","volume":"92","author":[{"given":"Jing","family":"Zhao","sequence":"first","affiliation":[{"name":"Tsinghua University , , ,","place":["Beijing, China, 100084"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaobo","family":"Xie","sequence":"additional","affiliation":[{"name":"Tsinghua University , , ,","place":["Beijing, China, 100084"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiaohong","family":"Lin","sequence":"additional","affiliation":[{"name":"Tsinghua University , , ,","place":["Beijing, China, 100084"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoxiao","family":"Ma","sequence":"additional","affiliation":[{"name":"Tsinghua University , , ,","place":["Beijing, China, 100084"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6148-0181","authenticated-orcid":true,"given":"Pei","family":"Su","sequence":"additional","affiliation":[{"name":"Purdue University , , 560 Oval Drive , , ,","place":["West Lafayette, Indiana, United States, 47907"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8694-9900","authenticated-orcid":true,"given":"Yu","family":"Xia","sequence":"additional","affiliation":[{"name":"Tsinghua University , , ,","place":["Beijing, China, 100084"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,8,25]]},"reference":[{"key":"2026081803324356100_cit1","doi-asserted-by":"publisher","first-page":"281","DOI":"10.1038\/nrm.2017.138","article-title":"Understanding the diversity\nof membrane lipid composition","volume":"19","author":"Harayama","year":"2018","journal-title":"Nat. Rev. Mol.\nCell Biol."},{"key":"2026081803324356100_cit2","doi-asserted-by":"publisher","first-page":"644","DOI":"10.1038\/s41589-020-0529-6","article-title":"Plasma Membranes\nare Asymmetric in Lipid Unsaturation, Packing and Protein Shape","volume":"16","author":"Lorent","year":"2020","journal-title":"Nat. Chem. Biol."},{"key":"2026081803324356100_cit3","doi-asserted-by":"publisher","first-page":"886","DOI":"10.1016\/j.devcel.2012.10.009","article-title":"Curvature, Lipid Packing,\nand Electrostatics of Membrane\nOrganelles: Defining Cellular Territories in Determining Specificity","volume":"23","author":"Bigay","year":"2012","journal-title":"Dev. Cell"},{"key":"2026081803324356100_cit4","doi-asserted-by":"publisher","first-page":"1668","DOI":"10.1016\/j.cell.2015.05.045","article-title":"A Global Map of\nLipid-Binding Proteins and Their Ligandability in Cells","volume":"161","author":"Niphakis","year":"2015","journal-title":"Cell"},{"key":"2026081803324356100_cit5","doi-asserted-by":"publisher","first-page":"403","DOI":"10.1038\/s41586-019-0904-1","article-title":"Evidence for an\nAlternative Fatty Acid Desaturation Pathway Increasing Cancer Plasticity","volume":"566","author":"Vriens","year":"2019","journal-title":"Nature"},{"key":"2026081803324356100_cit6","doi-asserted-by":"publisher","first-page":"755","DOI":"10.1038\/nchembio.2141","article-title":"Photoswitchable Diacylglycerols\nEnable Optical Control of Protein Kinase C","volume":"12","author":"Frank","year":"2016","journal-title":"Nat. Chem. Biol."},{"key":"2026081803324356100_cit7","doi-asserted-by":"publisher","first-page":"374","DOI":"10.1021\/acs.analchem.7b04836","article-title":"Analytical Challenges\nand Recent Advances in Mass Spectrometry\nBased Lipidomics","volume":"90","author":"Rustam","year":"2018","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit8","doi-asserted-by":"publisher","first-page":"6492","DOI":"10.1002\/anie.201812698","article-title":"Reshaping Lipid\nBiochemistry by Pushing Barriers in Structural Lipidomics","volume":"58","author":"Porta\nSiegel","year":"2019","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081803324356100_cit9","doi-asserted-by":"publisher","first-page":"28","DOI":"10.1016\/j.aca.2019.01.043","article-title":"Tutorial on lipidomics","volume":"1061","author":"Wang","year":"2019","journal-title":"Anal. Chim. Acta"},{"key":"2026081803324356100_cit10","doi-asserted-by":"publisher","first-page":"303","DOI":"10.1021\/ac7017684","article-title":"Ozone-Induced Dissociation:\nElucidation of Double Bond\nPosition within Mass-Selected Lipid Ions","volume":"80","author":"Thomas","year":"2008","journal-title":"Anal.\nChem."},{"key":"2026081803324356100_cit11","doi-asserted-by":"publisher","first-page":"15681","DOI":"10.1021\/jacs.7b06416","article-title":"Pinpointing Double\nBond and sn-Positions in Glycerophospholipids via Hybrid 193 nm Ultraviolet\nPhotodissociation (UVPD) Mass Spectrometry","volume":"139","author":"Williams","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"2026081803324356100_cit12","doi-asserted-by":"publisher","first-page":"1516","DOI":"10.1021\/acs.analchem.6b03353","article-title":"Structural Characterization\nof Phosphatidylcholines\nUsing 193 nm Ultraviolet Photodissociation Mass Spectrometry","volume":"89","author":"Klein","year":"2017","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit13","doi-asserted-by":"publisher","first-page":"2525","DOI":"10.1021\/ac062055a","article-title":"Atmospheric Pressure\nCovalent Adduct Chemical Ionization\nTandem Mass Spectrometry for Double Bond Localization in Monoene-\nand Diene-Containing Triacylglycerols","volume":"79","author":"Xu","year":"2007","journal-title":"Anal.\nChem."},{"key":"2026081803324356100_cit14","doi-asserted-by":"publisher","first-page":"1219","DOI":"10.1021\/acs.analchem.9b04376","article-title":"Toward\nComplete Structure Elucidation\nof Glycerophospholipids in the Gas Phase through Charge Inversion\nIon\/Ion Chemistry","volume":"92","author":"Randolph","year":"2020","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit15","doi-asserted-by":"publisher","first-page":"9032","DOI":"10.1021\/acs.analchem.9b01333","article-title":"Generating Fatty\nAcid Profiles in the Gas Phase: Fatty Acid Identification and Relative\nQuantitation Using Ion\/Ion Charge Inversion Chemistry","volume":"91","author":"Randolph","year":"2019","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit16","doi-asserted-by":"publisher","first-page":"5837","DOI":"10.1021\/acs.analchem.5b01460","article-title":"Near-Complete Structural\nCharacterization of Phosphatidylcholines\nUsing Electron Impact Excitation of Ions from Organics","volume":"87","author":"Campbell","year":"2015","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit17","doi-asserted-by":"publisher","first-page":"204","DOI":"10.1039\/C3AN01712E","article-title":"Structural\nCharacterization of Glycerophospholipids\nby Combinations of Ozone- and Collision-induced Dissociation Mass\nSpectrometry: the Next Step Towards \u201cTop-down\u201d Lipidomics","volume":"139","author":"Pham","year":"2014","journal-title":"Analyst"},{"key":"2026081803324356100_cit18","doi-asserted-by":"publisher","first-page":"115330","DOI":"10.1016\/j.trac.2018.11.028","article-title":"Novel strategies for\nenhancing shotgun lipidomics for comprehensive analysis of cellular\nlipidomes","volume":"120","author":"Hu","year":"2019","journal-title":"TrAC, Trends Anal. Chem."},{"key":"2026081803324356100_cit19","doi-asserted-by":"publisher","first-page":"1596","DOI":"10.1021\/acs.accounts.6b00030","article-title":"Chemical Derivatization and Ultrahigh\nResolution and\nAccurate Mass Spectrometry Strategies for \u201cShotgun\u201d\nLipidome Analysis","volume":"49","author":"Ryan","year":"2016","journal-title":"Acc. Chem. Res."},{"key":"2026081803324356100_cit20","doi-asserted-by":"publisher","first-page":"5013","DOI":"10.1021\/ac0702185","article-title":"Elucidation of Double\nBond Position in Unsaturated\nLipids by Ozone Electrospray Ionization Mass Spectrometry","volume":"79","author":"Thomas","year":"2007","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit21","doi-asserted-by":"publisher","first-page":"7345","DOI":"10.1021\/ac401242z","article-title":"Identification of Conjugated Linoleic\nAcid (CLA) Isomers\nby Silver Ion-Liquid Chromatography\/In-line Ozonolysis\/Mass Spectrometry\n(Ag+-LC\/O3-MS)","volume":"85","author":"Sun","year":"2013","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit22","doi-asserted-by":"publisher","first-page":"1915","DOI":"10.1021\/acs.analchem.7b04007","article-title":"Determining\nDouble Bond Position in Lipids Using Online Ozonolysis Coupled to\nLiquid Chromatography and Ion Mobility-Mass Spectrometry","volume":"90","author":"Harris","year":"2018","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit23","doi-asserted-by":"publisher","first-page":"481","DOI":"10.1007\/s13361-017-1861-2","article-title":"UV Lamp as\na Facile Ozone Source\nfor Structural Analysis of Unsaturated Lipids Via Electrospray Ionization-Mass\nSpectrometry","volume":"29","author":"Stinson","year":"2018","journal-title":"J. Am. Soc. Mass Spectrom."},{"key":"2026081803324356100_cit24","doi-asserted-by":"publisher","first-page":"2592","DOI":"10.1002\/anie.201310699","article-title":"Pinpointing Double\nBonds in Lipids by Paterno\u0300-Bu\u0308chi\nReactions and Mass Spectrometry","volume":"53","author":"Ma","year":"2014","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026081803324356100_cit25","doi-asserted-by":"publisher","first-page":"10286","DOI":"10.1021\/acs.analchem.8b02021","article-title":"Locating Carbon\u2013Carbon\nDouble Bonds in Unsaturated Phospholipids by Epoxidation Reaction\nand Tandem Mass Spectrometry","volume":"90","author":"Cao","year":"2018","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit26","doi-asserted-by":"publisher","first-page":"11905","DOI":"10.1021\/acs.analchem.9b02667","article-title":"Deep Lipidomics\nand Molecular Imaging\nof Unsaturated Lipid Isomers: A Universal Strategy Initiated by mCPBA\nEpoxidation","volume":"91","author":"Kuo","year":"2019","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit27","doi-asserted-by":"publisher","first-page":"209","DOI":"10.1002\/anie.201911070","article-title":"On-Demand Electrochemical\nEpoxidation\nin Nano-Electrospray Ionization Mass Spectrometry to Locate Carbon\u2013Carbon\nDouble Bonds","volume":"59","author":"Tang","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081803324356100_cit28","doi-asserted-by":"publisher","first-page":"2573","DOI":"10.1073\/pnas.1523356113","article-title":"Identification and Quantitation of\nLipid C\ue5fbC Location Isomers: A Shotgun Lipidomics Approach Enabled\nby Photochemical Reaction","volume":"113","author":"Ma","year":"2016","journal-title":"Proc. Natl. Acad.\nSci."},{"key":"2026081803324356100_cit29","doi-asserted-by":"publisher","first-page":"3696","DOI":"10.1039\/C6AN00015K","article-title":"A Method of Coupling the Paterno\u0300\u2013Bu\u0308chi\nReaction\nwith Direct Infusion ESI-MS\/MS for Locating the C\ue5fbC Bond in\nGlycerophospholipids","volume":"141","author":"Stinson","year":"2016","journal-title":"Analyst"},{"key":"2026081803324356100_cit30","doi-asserted-by":"publisher","first-page":"4739","DOI":"10.1007\/s00216-018-1537-1","article-title":"In-depth structural\ncharacterization of phospholipids by pairing solution photochemical\nreaction with charge inversion ion\/ion chemistry","volume":"411","author":"Franklin","year":"2019","journal-title":"Anal. Bioanal. Chem."},{"key":"2026081803324356100_cit31","doi-asserted-by":"publisher","first-page":"116206","DOI":"10.1016\/j.ijms.2019.116206","article-title":"Mapping Lipid\nC\ue5fbC Location Isomers in Organ Tissues by Coupling Photochemical\nDerivatization and Rapid Extractive Mass Spectrometry","volume":"445","author":"Su","year":"2019","journal-title":"Int. J. Mass Spectrom."},{"key":"2026081803324356100_cit32","doi-asserted-by":"publisher","first-page":"6064","DOI":"10.1002\/anie.201900011","article-title":"A Polymer Coating Transfer\nEnrichment Method for Direct\nMass Spectrometry Analysis of Lipids in Biofluid Samples","volume":"58","author":"Zhang","year":"2019","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081803324356100_cit33","doi-asserted-by":"publisher","first-page":"79","DOI":"10.1038\/s41467-018-07963-8","article-title":"Online Photochemical Derivatization Enables Comprehensive Mass Spectrometric\nAnalysis of Unsaturated Phospholipid Isomers","volume":"10","author":"Zhang","year":"2019","journal-title":"Nat. Commun."},{"key":"2026081803324356100_cit34","doi-asserted-by":"publisher","first-page":"6719","DOI":"10.1021\/acs.analchem.0c00690","article-title":"Enhanced Phospholipid\nIsomer Analysis by Online Photochemical Derivatization and RPLC-MS","volume":"92","author":"Zhang","year":"2020","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit35","doi-asserted-by":"publisher","first-page":"10740","DOI":"10.1039\/C9SC03521D","article-title":"A Lipidomic\nWorkflow\nCapable of Resolving sn- and C\ue5fbC Location Isomers of Phosphatidylcholines","volume":"10","author":"Zhao","year":"2019","journal-title":"Chem. Sci."},{"key":"2026081803324356100_cit36","doi-asserted-by":"publisher","first-page":"513","DOI":"10.1039\/C9AN01515A","article-title":"Analysis of\nEther Glycerophosphocholines\nat the Level of C\ue5fbC Locations from Human Plasma","volume":"145","author":"Lin","year":"2020","journal-title":"Analyst"},{"key":"2026081803324356100_cit37","doi-asserted-by":"publisher","first-page":"12092","DOI":"10.1002\/anie.201806635","article-title":"An On-Tissue\nPaterno\u0300\u2013Bu\u0308chi Reaction for Localization of Carbon\u2013Carbon\nDouble Bonds in Phospholipids and Glycolipids by Matrix-Assisted Laser-Desorption\u2013Ionization\nMass-Spectrometry Imaging","volume":"57","author":"Bednar\u030ci\u0301k","year":"2018","journal-title":"Angew. Chem., Int.\nEd."},{"key":"2026081803324356100_cit38","doi-asserted-by":"publisher","first-page":"11816","DOI":"10.1021\/jacs.9b05868","article-title":"Reactive Matrix-Assisted\nLaser Desorption\/Ionization\nMass Spectrometry Imaging Using an Intrinsically Photoreactive Paterno\u0300\u2013Bu\u0308chi\nMatrix for Double-Bond Localization in Isomeric Phospholipids","volume":"141","author":"Wa\u0308ldchen","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"2026081803324356100_cit39","doi-asserted-by":"publisher","first-page":"700","DOI":"10.1007\/BF00659226","article-title":"Effect of Temperature and Salts on the UV Absorption\nSpectra of Acetone and Methylethylketone","volume":"9","author":"Pominov","year":"1968","journal-title":"J.\nAppl. Spectrosc."},{"key":"2026081803324356100_cit40","doi-asserted-by":"publisher","first-page":"4744","DOI":"10.1039\/C7AN01158J","article-title":"Selective\nPhosphatidylcholine Double Bond Fragmentation and Localisation Using\nPaterno\u0300\u2013Bu\u0308chi Reactions and Ultraviolet Photodissociation","volume":"142","author":"Wa\u0308ldchen","year":"2017","journal-title":"Analyst"},{"key":"2026081803324356100_cit41","doi-asserted-by":"publisher","first-page":"1971","DOI":"10.1007\/s13361-018-2023-x","article-title":"Charging and Charge\nSwitching of Unsaturated Lipids\nand Apolar Compounds Using Paterno\u0300-Bu\u0308chi Reactions","volume":"29","author":"Esch","year":"2018","journal-title":"J. Am. Soc. Mass Spectrom."},{"key":"2026081803324356100_cit42","doi-asserted-by":"publisher","first-page":"2256","DOI":"10.1039\/C9AN02260K","article-title":"Investigating C\ue5fbC Positions\nand Hydroxylation\nSites in Lipids Using Paterno\u0300\u2013Bu\u0308chi Functionalization\nMass Spectrometry","volume":"145","author":"Esch","year":"2020","journal-title":"Analyst"},{"key":"2026081803324356100_cit43","doi-asserted-by":"publisher","first-page":"375","DOI":"10.1038\/s41467-019-14180-4","article-title":"Large-scale\nLipid Analysis with C\ue5fbC Location and sn-position Isomer Resolving\nPower","volume":"11","author":"Cao","year":"2020","journal-title":"Nat. Commun."},{"key":"2026081803324356100_cit44","doi-asserted-by":"publisher","first-page":"83","DOI":"10.1016\/j.jphotochemrev.2017.10.002","article-title":"The Paterno\u0300-Bu\u0308chi Reaction\ue5f8Mechanisms\nand Application to Organic Synthesis","volume":"33","author":"Fre\u0301neau","year":"2017","journal-title":"J. Photoch.\nPhotobio. C."},{"key":"2026081803324356100_cit45","doi-asserted-by":"publisher","first-page":"1523","DOI":"10.1194\/jlr.M033506","article-title":"Shorthand\nNotation for Lipid Structures Derived from Mass Spectrometry","volume":"54","author":"Liebisch","year":"2013","journal-title":"J. Lipid Res."},{"key":"2026081803324356100_cit46","doi-asserted-by":"publisher","first-page":"119","DOI":"10.1021\/cr300177k","article-title":"Photoremovable\nProtecting Groups in Chemistry and Biology: Reaction Mechanisms and\nEfficacy","volume":"113","author":"Kla\u0301n","year":"2013","journal-title":"Chem. Rev."},{"key":"2026081803324356100_cit47","doi-asserted-by":"publisher","first-page":"165","DOI":"10.1021\/cr00002a004","article-title":"A survey of Hammett substituent constants and resonance\nand field parameters","volume":"91","author":"Hansch","year":"1991","journal-title":"Chem. Rev."},{"key":"2026081803324356100_cit48","doi-asserted-by":"publisher","first-page":"134305","DOI":"10.1063\/1.4869802","article-title":"Triplet State Photochemistry and the Three-state Crossing\nof Acetophenone within Time-dependent Density-functional Theory","volume":"140","author":"Huix-Rotllant","year":"2014","journal-title":"J. Chem. Phys."},{"key":"2026081803324356100_cit49","doi-asserted-by":"publisher","first-page":"50","DOI":"10.1016\/j.crci.2015.10.002","article-title":"Population of Triplet States in Acetophenone:\nA Quantum Dynamics Perspective","volume":"19","author":"Huix-Rotllant","year":"2016","journal-title":"C. R. Chim."},{"key":"2026081803324356100_cit50","doi-asserted-by":"publisher","first-page":"9201","DOI":"10.1002\/anie.201004571","article-title":"Ordering,\nInteraction, and Reactivity of the Low-Lying n\u03c0* and \u03c0\u03c0*\nExcited Triplet States of Acetophenone Derivatives","volume":"49","author":"Yabumoto","year":"2010","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081803324356100_cit51","doi-asserted-by":"publisher","first-page":"10188","DOI":"10.1021\/acs.joc.7b01698","article-title":"Steric Scale of Common Substituents from Rotational\nBarriers of N-(o-Substituted aryl)\u00adthiazoline-2-thione Atropisomers","volume":"82","author":"Belot","year":"2017","journal-title":"J. Org. Chem."},{"key":"2026081803324356100_cit52","doi-asserted-by":"publisher","first-page":"41","DOI":"10.1021\/ar50086a001","article-title":"Classification of Photochemical Reactions","volume":"8","author":"Dauben","year":"1975","journal-title":"Acc. Chem. Res."},{"key":"2026081803324356100_cit53","doi-asserted-by":"publisher","first-page":"7173","DOI":"10.1021\/acs.analchem.9b00374","article-title":"Analysis of Conjugated\nFatty Acid Isomers by the Paterno\u0300-Bu\u0308chi\nReaction and Trapped Ion Mobility Mass Spectrometry","volume":"91","author":"Xie","year":"2019","journal-title":"Anal. Chem."},{"key":"2026081803324356100_cit54","doi-asserted-by":"publisher","first-page":"9102","DOI":"10.1021\/acs.analchem.9b01584","article-title":"Benzophenone\nPhotoreactivity in a Lipid Bilayer To Probe Peptide\/Membrane Interactions:\nSimple System","volume":"91","author":"Bechtella","year":"2019","journal-title":"Complex Information. Anal. Chem."},{"key":"2026081803324356100_cit55","doi-asserted-by":"publisher","first-page":"8226","DOI":"10.1002\/anie.201703465","article-title":"Exploiting Benzophenone\nPhotoreactivity\nTo Probe the Phospholipid Environment and Insertion Depth of the Cell-Penetrating\nPeptide Penetratin in Model Membranes","volume":"56","author":"Jiao","year":"2017","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026081803324356100_cit56","doi-asserted-by":"publisher","first-page":"8931","DOI":"10.1021\/acs.analchem.6b02834","article-title":"Photochemical\nTagging for Quantitation\nof Unsaturated Fatty Acids by Mass Spectrometry","volume":"88","author":"Ma","year":"2016","journal-title":"Anal. Chem."}],"container-title":["Analytical\nChemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.analchem.0c02896","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/ancham\/article-pdf\/92\/19\/13470\/8597704\/ac0c02896.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/ancham\/article-pdf\/92\/19\/13470\/8597704\/ac0c02896.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T08:59:24Z","timestamp":1787043564000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/ancham\/article\/92\/19\/13470\/828654\/Next-Generation-Paterno-Bu-chi-Reagents-for-Lipid"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,8,25]]},"references-count":56,"journal-issue":{"issue":"19","published-online":{"date-parts":[[2020,8,25]]},"published-print":{"date-parts":[[2020,10,6]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.analchem.0c02896","relation":{},"ISSN":["0003-2700","1520-6882"],"issn-type":[{"value":"0003-2700","type":"print"},{"value":"1520-6882","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,8,25]]}}}