{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T17:16:46Z","timestamp":1788455806918,"version":"build-2803163510"},"reference-count":31,"publisher":"American Chemical Society (ACS)","issue":"9","license":[{"start":{"date-parts":[[2026,8,13]],"date-time":"2026-08-13T00:00:00Z","timestamp":1786579200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,13]],"date-time":"2026-08-13T00:00:00Z","timestamp":1786579200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,13]],"date-time":"2026-08-13T00:00:00Z","timestamp":1786579200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE-2304386"],"award-info":[{"award-number":["CHE-2304386"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,2]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Bis(monoacylglycero)phosphates (BMPs) and phosphatidylglycerols (PGs) constitute a unique class of lipid regioisomers with distinct structural features and biochemical roles. However, ion trap collision-induced dissociation (IT-CID) alone is insufficient to differentiate isomeric deprotonated PG and BMP ions. Herein, we describe a gas-phase charge-inversion ion\/ion reaction that generates an ion type enabling straightforward, unambiguous differentiation of BMP and PG isomers upon IT-CID. The approach involves charge inversion of isomeric, deprotonated BMP or PG anions using the dicationic magnesium 4,4\u2032,4\u2033-tri-tert-butyl-2,2\u2032:6\u2032,2\u2033-terpyridine complex ([Mg(ttbt)2]2+), followed by IT-CID to produce diagnostic fragment ions indicative of each isomer. These fragment ions arise from even-electron charge remote fragmentation (CRF) pathways. Subsequent MSn experiments involving fatty acid fragment ions complexed with [Mg(ttbt)2]2+ proceed through odd-electron radical directed dissociation (RDD), providing detailed information on acyl chain carbon\u2013carbon double bond position(s). Ion types generated via negative ion mode nESI and through ion\/ion reactions were applied to distinguish targeted PG and BMP isomers at the carbon\u2013carbon double bond positional level in a mouse liver extract using a shotgun lipidomics approach.<\/jats:p>","DOI":"10.1021\/jasms.6c00236","type":"journal-article","created":{"date-parts":[[2026,8,13]],"date-time":"2026-08-13T13:02:06Z","timestamp":1786626126000},"page":"2192-2200","source":"Crossref","is-referenced-by-count":1,"title":["Differentiation of\nIsomeric Bis(monoacylglycero)phosphates\nand Phosphatidylglycerols via Gas-Phase Ion\/Ion Reactions and Ion\nTrap Collision-Induced Dissociation"],"prefix":"10.1021","volume":"37","author":[{"ORCID":"https:\/\/orcid.org\/0009-0004-8819-3878","authenticated-orcid":true,"given":"Rebekah G.","family":"Bogle","sequence":"first","affiliation":[{"name":"Purdue University , , 560 Oval Drive , , ,","place":["West Lafayette, Indiana, United States, 47907-2084"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sarah T.","family":"Nsiah","sequence":"additional","affiliation":[{"name":"Purdue University , , 560 Oval Drive , , ,","place":["West Lafayette, Indiana, United States, 47907-2084"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"De\u2019Shovon M.","family":"Shenault","sequence":"additional","affiliation":[{"name":"Purdue University , , 560 Oval Drive , , ,","place":["West Lafayette, Indiana, United States, 47907-2084"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-2117-3522","authenticated-orcid":true,"given":"Katherine A.","family":"Walker","sequence":"additional","affiliation":[{"name":"Purdue University , , 560 Oval Drive , , ,","place":["West Lafayette, Indiana, United States, 47907-2084"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Caitlin E.","family":"Randolph","sequence":"additional","affiliation":[{"name":"Purdue University , , 560 Oval Drive , , ,","place":["West Lafayette, Indiana, United States, 47907-2084"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1648-5570","authenticated-orcid":true,"given":"Scott A.","family":"McLuckey","sequence":"additional","affiliation":[{"name":"Purdue University , , 560 Oval Drive , , ,","place":["West Lafayette, Indiana, United States, 47907-2084"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,13]]},"reference":[{"issue":"2","key":"2026090311505843900_cit1","doi-asserted-by":"publisher","DOI":"10.1002\/jimd.70019","article-title":"Glycerophospholipids: Roles in Cell\nTrafficking and Associated Inborn Errors","volume":"48","author":"Lamari","year":"2025","journal-title":"J.\nInherited Metab. Dis."},{"issue":"1","key":"2026090311505843900_cit2","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1007\/s12154-016-0159-3","article-title":"Is Phosphatidylglycerol\nEssential for Terrestrial Life?","volume":"10","author":"Furse","year":"2017","journal-title":"J. Chem. Biol."},{"issue":"21","key":"2026090311505843900_cit3","doi-asserted-by":"publisher","DOI":"10.3390\/ijms21218067","article-title":"The Emerging and Diverse Roles of Bis(Monoacylglycero) Phosphate\nLipids in Cellular Physiology and Disease","volume":"21","author":"Showalter","year":"2020","journal-title":"Int.\nJ. Mol. Sci."},{"issue":"5\u20136","key":"2026090311505843900_cit4","doi-asserted-by":"publisher","first-page":"313","DOI":"10.1016\/j.plefa.2009.09.006","article-title":"Bis(Monoacylglycero)Phosphate,\na Peculiar Phospholipid to Control the Fate of Cholesterol: Implications\nin Pathology","volume":"81","author":"Hullin-Matsuda","year":"2009","journal-title":"Prostaglandins, Leukotrienes Essent.\nFatty Acids"},{"key":"2026090311505843900_cit5","doi-asserted-by":"publisher","first-page":"189","DOI":"10.1016\/0006-3002(58)90308-1","article-title":"Plant Phospholipids I. Identification\nof the Phosphatidyl Glycerols","volume":"27","author":"Benson","year":"1958","journal-title":"Biochim. Biophys.\nActa"},{"key":"2026090311505843900_cit6","doi-asserted-by":"publisher","first-page":"255","DOI":"10.1016\/j.ijms.2014.08.026","article-title":"Ion Mobility\nand Tandem Mass Spectrometry of Phosphatidylglycerol and Bis(Monoacylglycerol)Phosphate\n(BMP)","volume":"378","author":"Hankin","year":"2015","journal-title":"Int. J. Mass Spectrom."},{"key":"2026090311505843900_cit7","first-page":"77","article-title":"Quantitative Analysis\nof Polyphosphoinositide,\nBis(Monoacylglycero)Phosphate and Phosphatidylglycerol Species by\nShotgun Lipidomics after Methylation","volume-title":"Methods\nin Molecular Biology","author":"Pan","year":"2021"},{"issue":"16","key":"2026090311505843900_cit8","doi-asserted-by":"publisher","first-page":"8490","DOI":"10.1021\/acs.analchem.7b02058","article-title":"Strategy for Quantitative\nAnalysis of Isomeric Bis(Monoacylglycero)Phosphate and Phosphatidylglycerol\nSpecies by Shotgun Lipidomics after One-Step Methylation","volume":"89","author":"Wang","year":"2017","journal-title":"Anal. Chem."},{"key":"2026090311505843900_cit9","doi-asserted-by":"publisher","first-page":"105","DOI":"10.1016\/j.chroma.2018.06.039","article-title":"Separation and Identification\nof Phospholipids by Hydrophilic Interaction Liquid Chromatography\nCoupled to Tandem High Resolution Mass Spectrometry with Focus on\nIsomeric Phosphatidylglycerol and Bis(Monoacylglycero)Phosphate","volume":"1565","author":"Vosse","year":"2018","journal-title":"J. Chromatogr. A"},{"issue":"21","key":"2026090311505843900_cit10","doi-asserted-by":"publisher","first-page":"8794","DOI":"10.1021\/ac1021826","article-title":"Simultaneous Quantification\nof Cardiolipin,\nBis(Monoacylglycero)Phosphate and Their Precursors by Hydrophilic\nInteraction LC\u2013MS\/MS Including Correction of Isotopic Overlap","volume":"82","author":"Scherer","year":"2010","journal-title":"Anal. Chem."},{"key":"2026090311505843900_cit11","doi-asserted-by":"publisher","first-page":"7","DOI":"10.1016\/j.jmsacl.2021.12.005","article-title":"Lipid Analysis\nby Ion Mobility Spectrometry Combined with Mass Spectrometry: A Brief\nUpdate with a Perspective on Applications in the Clinical Laboratory","volume":"23","author":"Dubland","year":"2022","journal-title":"J. Mass Spectrom. Adv. Clin. Lab"},{"key":"2026090311505843900_cit12","doi-asserted-by":"publisher","first-page":"111","DOI":"10.1016\/j.cbpa.2017.11.009","article-title":"Recent\nAdvances in Lipid Separations\nand Structural Elucidation Using Mass Spectrometry Combined with Ion\nMobility Spectrometry, Ion\u2013Molecule Reactions and Fragmentation\nApproaches","volume":"42","author":"Zheng","year":"2018","journal-title":"Curr. Opin. Chem. Biol."},{"key":"2026090311505843900_cit13","doi-asserted-by":"publisher","first-page":"60","DOI":"10.1016\/j.aca.2019.07.060","article-title":"Quantitative Molecular\nTissue Atlas of Bis(Monoacylglycero)Phosphate and Phosphatidylglycerol\nMembrane Lipids in Rodent Organs Generated by Methylation Assisted\nHigh Resolution Mass Spectrometry","volume":"1084","author":"Wang","year":"2019","journal-title":"Anal. Chim.\nActa"},{"issue":"16","key":"2026090311505843900_cit14","doi-asserted-by":"publisher","first-page":"3665","DOI":"10.1007\/s00216-025-05890-4","article-title":"Label-Free Quantitative Shotgun Analysis\nof Bis(Monoacylglycero)Phosphate Lipids","volume":"417","author":"Wang","year":"2025","journal-title":"Anal.\nBioanal. Chem."},{"issue":"17","key":"2026090311505843900_cit15","doi-asserted-by":"publisher","first-page":"8732","DOI":"10.1021\/acs.analchem.5b01536","article-title":"Charge-inversion\nof Phospholipids\nby Dimetal Complexes for Positive Ion-Mode Electrospray Ionization\nMass Spectrometry Analysis","volume":"87","author":"Svane","year":"2015","journal-title":"Anal. Chem."},{"issue":"19","key":"2026090311505843900_cit16","doi-asserted-by":"publisher","first-page":"13387","DOI":"10.1021\/acs.analchem.0c02755","article-title":"Differentiation and Quantification of Diastereomeric\nPairs of Glycosphingolipids Using Gas-Phase Ion Chemistry","volume":"92","author":"Chao","year":"2020","journal-title":"Anal. Chem."},{"issue":"1","key":"2026090311505843900_cit17","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."},{"issue":"5","key":"2026090311505843900_cit18","doi-asserted-by":"publisher","first-page":"1093","DOI":"10.1021\/jasms.0c00025","article-title":"Structural Elucidation\nof Ether Glycerophospholipids Using Gas-Phase Ion\/Ion Charge-inversion\nChemistry","volume":"31","author":"Randolph","year":"2020","journal-title":"J. Am. Soc. Mass Spectrom."},{"issue":"9","key":"2026090311505843900_cit19","doi-asserted-by":"publisher","first-page":"1868","DOI":"10.1021\/jasms.3c00081","article-title":"Separation of Isobaric Lipids in Imaging Mass Spectrometry\nUsing Gas-Phase Charge-inversion Ion\/Ion Reactions","volume":"34","author":"Specker","year":"2023","journal-title":"J. Am. Soc. Mass Spectrom."},{"issue":"6","key":"2026090311505843900_cit20","doi-asserted-by":"publisher","first-page":"1476","DOI":"10.1021\/jasms.6c00068","article-title":"Manipulation\nof Gas-Phase Charge\nInversion Ion\/Ion Reaction Kinetics for Improved Phospholipid Identification\nin Imaging Mass Spectrometry","volume":"37","author":"Guo","year":"2026","journal-title":"J. Am. Soc. Mass\nSpectrom."},{"issue":"8","key":"2026090311505843900_cit21","doi-asserted-by":"publisher","first-page":"1797","DOI":"10.1021\/jasms.4c00144","article-title":"Enhancing Spatial Resolution in Tandem\nMass Spectrometry Ion\/Ion Reaction Imaging Experiments through Image\nFusion","volume":"35","author":"Liang","year":"2024","journal-title":"J. Am. Soc. Mass Spectrom."},{"issue":"21","key":"2026090311505843900_cit22","doi-asserted-by":"publisher","first-page":"12861","DOI":"10.1021\/acs.analchem.8b03441","article-title":"Gas-Phase\nIon\/Ion Reactions Involving Tris-Phenanthroline Alkaline Earth Metal\nComplexes as Charge-inversion Reagents for the Identification of Fatty\nAcids","volume":"90","author":"Randolph","year":"2018","journal-title":"Anal. Chem."},{"issue":"11","key":"2026090311505843900_cit23","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.9741","article-title":"Structural Characterization of Fatty\nAcid Anions via Gas-phase Charge Inversion Using Mg(Tri-butyl-terpyridine)22+\nReagent Ions","volume":"38","author":"Nsiah","year":"2024","journal-title":"Rapid Commun. Mass Spectrom."},{"issue":"26","key":"2026090311505843900_cit24","doi-asserted-by":"publisher","first-page":"8098","DOI":"10.1039\/c2dt12426b","article-title":"Synthesis and Computational\nStudies of Mg Complexes Supported by 2,2\u2032:6,2\u2033-Terpyridine\nLigands","volume":"41","author":"Guard","year":"2012","journal-title":"Dalton Trans."},{"key":"2026090311505843900_cit25","doi-asserted-by":"publisher","first-page":"71","DOI":"10.1016\/j.jasms.2004.09.017","article-title":"Mutual Storage Mode\nIon\/Ion Reactions in Hybrid Linear Ion Trap","volume":"16","author":"Xia","year":"2005","journal-title":"J. Am. Soc. Mass Spectrom."},{"key":"2026090311505843900_cit26","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijms.2022.116874","article-title":"Adaptation\nand Operation of a Quadrupole\/Time-of-Flight Tandem Mass Spectrometer\nfor High Mass Ion\/Ion Reaction Studies","volume":"478","author":"Bhanot","year":"2022","journal-title":"Int.\nJ. Mass Spectrom."},{"issue":"10","key":"2026090311505843900_cit27","doi-asserted-by":"publisher","first-page":"1130","DOI":"10.1016\/S1044-0305(03)00446-X","article-title":"Mass selective axial\nejection from a linear quadrupole\nion trap","volume":"14","author":"Londry","year":"2003","journal-title":"J. Am. Soc. Mass Spectrom."},{"issue":"14","key":"2026090311505843900_cit28","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."},{"issue":"7","key":"2026090311505843900_cit29","doi-asserted-by":"publisher","first-page":"805","DOI":"10.1002\/rcm.6503","article-title":"Rapid Differentiation\nof Isomeric Lipids by Photodissociation Mass Spectrometry of Fatty\nAcid Derivatives","volume":"27","author":"Pham","year":"2013","journal-title":"Rapid Commun. Mass Spectrom."},{"issue":"8","key":"2026090311505843900_cit30","doi-asserted-by":"publisher","first-page":"1688","DOI":"10.1007\/s13361-018-1993-z","article-title":"Characterization of Long-Chain Fatty\nAcid as N-(4-Aminomethylphenyl) Pyridinium Derivative by MALDI LIFT-TOF\/TOF\nMass Spectrometry","volume":"29","author":"Frankfater","year":"2018","journal-title":"J. Am. Soc. Mass Spectrom."},{"key":"2026090311505843900_cit31","doi-asserted-by":"publisher","first-page":"9312","DOI":"10.1021\/ac402078p","article-title":"Fatty Acidomics:\nGlobal Analysis\nof Lipid Species Containing a Carboxyl Group with a Charge-Remote\nFragmentation-Assisted Approach","volume":"85","author":"Wang","year":"2013","journal-title":"Anal. Chem."}],"container-title":["Journal of the American\nSociety for Mass Spectrometry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jasms.6c00236","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jamsef\/article-pdf\/37\/9\/2192\/66523288\/jasms.6c00236.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jamsef\/article-pdf\/37\/9\/2192\/66523288\/jasms.6c00236.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T16:22:16Z","timestamp":1788452536000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jamsef\/article\/37\/9\/2192\/5254174\/Differentiation-of-Isomeric-Bis-monoacylglycero"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,13]]},"references-count":31,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2026,8,13]]},"published-print":{"date-parts":[[2026,9,2]]}},"URL":"https:\/\/doi.org\/10.1021\/jasms.6c00236","relation":{},"ISSN":["1044-0305","1879-1123"],"issn-type":[{"value":"1044-0305","type":"print"},{"value":"1879-1123","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,13]]}}}