Ion–Molecule Reactions: Analytical and Structural Tool

Osburn, Sandra; Ryzhov, Victor

doi:10.1021/ac302920a

Cited by 59 publications

(74 citation statements)

References 126 publications

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“…These reactions have been previously reviewed. 97,102,103,117–119 Conventional radical cations predominantly undergo electron or proton transfer reactions. Unlike their conventional counterparts, distonic radical contain spatially separated charge and radical sites, and electron transfer reactions are typically not observed due to the low recombination energies of their charged sites.…”

Section: Ion Structure Determinationmentioning

confidence: 99%

Properties and Reactivity of Gaseous Distonic Radical Ions with Aryl Radical Sites

et al. 2013

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Section: Ion Structure Determinationmentioning

confidence: 99%

Properties and Reactivity of Gaseous Distonic Radical Ions with Aryl Radical Sites

et al. 2013

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“…(Brodbelt, 1997;Watkins et al, 2004Watkins et al, , 2005Eberlin, 2006;Fu et al, 2012;Osburn and Ryzhov, 2013). Several neutral reagents for GPIMR such as dimethyl disulfide (DMDS), tert-butyl peroxide (TBP), and tri (dimethylamino)borane (TDMAB) have been developed to identify oxidized heteroatom functionalities (Watkins et al, 2005;Duan et al, 2008Duan et al, , 2009Fu et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Identification of 2-Aminothiazolobenzazepine Metabolites in Human, Rat, Dog, and Monkey Microsomes by Ion-Molecule Reactions in Linear Quadrupole Ion Trap Mass Spectrometry

et al. 2014

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2-Aminothiazolobenzazepine (2-ATBA), 7-[(1-methyl-1H-pyrazol-4-yl)methyl]-6,7,8,9-tetrahydro-5H-[1,3]thiazolo[4,5-h][3]benzazepin-2-amine, is a D2 partial agonist that has demonstrated antipsychotic effects in a rodent in vivo efficacy model. The metabolite profile showed that 2-ATBA is mainly metabolized by oxidation. However, identification of the oxidation site(s) in the 2-aminothiazole group presents a challenge for the traditional metabolite identification methods such as liquid chromatography/mass spectrometry and NMR due to the lack of unique tandem mass spectrometry fragmentation patterns for ions with the 2-aminothiazole group oxidized at different sites and the lack of stability for purification or reference standard synthesis. We describe the characterization of the oxidized heteroatoms of the 2-aminothiazole group via gas-phase ion-molecule reactions (GPIMR) in a modified linear quadrupole ion trap mass spectrometer. The GPIMR reagents used were dimethyl disulfide, tert-butyl peroxide, and tri(dimethylamino)borane. Each reagent was introduced into the ion trap through the helium line and was allowed to react with the protonated metabolites. The ionic ion-molecule reaction products and their fragmentation profiles were compared with the profiles of the ionic ion-molecule reaction products of protonated reference compounds that had specific heteroatom functionalities. The oxidized 2-aminothiazole metabolite of 2-ATBA showed a similar GPIMR profile to that of the reference compounds with a tertiary N-oxide functionality and distinct from the profiles of the reference compounds with N-aryl hydroxylamine, nitroso, or pyridine N-oxide functionalities. This study demonstrates the feasibility of fingerprinting the chemical nature of oxidized nitrogen functional groups via GPIMR profiling for metabolite structure elucidation.

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“…There are also many recent and important biologically relevant applications of ion/molecule reactions[2], including reactions with post-translational modifications of peptides[3, 4], isomers of phosphorylated sugars[5], gas phase hydrogen/deuterium exchange reactions[6, 7], and reactions of ozone with lipids[8]. The goal of these reactions is to reveal the different aspects of ion structure and to quantify changes in structure that cannot be probed by the “traditional” mass spectrometric methods of measuring molecular and/or fragment ion masses.…”

Section: Introductionmentioning

confidence: 99%

Design of a TW-SLIM Module for Dual Polarity Confinement, Transport, and Reactions

Garimella

Webb

Prabhakaran

et al. 2017

J. Am. Soc. Mass Spectrom.

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Here we describe instrumental approaches for performing dual polarity ion confinement, transport, ion mobility separations and reactions in Structures for Lossless Ion Manipulations (SLIM). Previous means of ion confinement in SLIM based upon rf- generated pseudopotentials and dc fields for lateral confinement cannot trap ions of opposite polarity simultaneously. Here we explore alternative approaches to provide lateral confinement of both ion polarities. Traveling wave ion mobility (IM) separations experienced by both polarities in such SLIM cause ions of both polarities to migrate in the same directions and exhibit similar separations. The ion motion (and relative motion of the two polarities) under both surfing and IM separation conditions are discussed. In surfing conditions, where the traveling wave speed is less than the ion velocity, the two polarities are transported losslessly and non-reactively in their respective potential minima (higher absolute voltage regions confines negative polarities and lower absolute potential regions are populated by positive polarities). In separation mode, where the traveling wave speed is greater than the ion velocity, the two polarities can interact during rollovers over the traveling wave. Strategies to minimize overlap of the two ion populations to prevent reactive losses during separations are presented. A theoretical treatment of the time scales over which two populations (injected into a dc field-free region of the dual polarity SLIM device) interact is considered, and SLIM designs for allowing ion/ion interactions and other manipulations with dual polarities at 4 torr are presented.

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Ion–Molecule Reactions: Analytical and Structural Tool

Cited by 59 publications

References 126 publications

Properties and Reactivity of Gaseous Distonic Radical Ions with Aryl Radical Sites

Properties and Reactivity of Gaseous Distonic Radical Ions with Aryl Radical Sites

Identification of 2-Aminothiazolobenzazepine Metabolites in Human, Rat, Dog, and Monkey Microsomes by Ion-Molecule Reactions in Linear Quadrupole Ion Trap Mass Spectrometry

Design of a TW-SLIM Module for Dual Polarity Confinement, Transport, and Reactions

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