Comparison of the Applicability of Mass Spectrometer Ion Sources Using a Polarity—Molecular Weight Scattergram with a 600-Sample In-House Chemical Library

Sugimura, Natsuhiko; Furuya, Asami; Yatsu, Takahiro; Shibue, Toshimichi

doi:10.1255/ejms.1345

Cited by 10 publications

(13 citation statements)

References 21 publications

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“…A chemical library was constructed by collecting samples submitted to our contracted HRMS measurement service. 15,17,18 The library samples were gathered from June 2012 to March 2013, and 611 samples were obtained. The identities of all the compounds in the sample library were confirmed by HRMS using ESI time-of-flight mass spectrometry (a few samples were confirmed using a FAB sector mass spectrometer) with errors of <5 ppm compared with the elemental compositions declared by the clients of the HRMS measurement service.…”

Section: Methodsmentioning

confidence: 99%

“…Previously, we investigated the applicabilities of DART, electrospray ionization (ESI), and fast atom bombardment (FAB) using the molecular weight (MW) and the topological polar surface area (tPSA) 14 as the molecular polarity. 15 According to that study, DART gave a better sample detection rate in the mass range below MW 800, therefore DART is not suitable for heavy compounds (MW > 800). It was concluded that DART has high potential in compensating for the weak performance areas of ESI.…”

Section: Introductionmentioning

confidence: 94%

“…The calculation details are given in our previous studies. 15,17 Results and discussion Observed DART adducts for in-house chemical library…”

Section: Calculation Of Tpsamentioning

confidence: 99%

“…Of the 588 samples, 566 samples were detected on positive mode DART. 15 The majority of observed ions were [M þ H] þ or [M þ NH 4 ] þ . However, eight compounds were detected as molecular-related ions of which, five compounds were detected as nonadducted ion presumed radical cation, remaining three compounds were detected as other molecular-related ions.…”

Section: Calculation Of Tpsamentioning

confidence: 99%

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Observed adducts on positive mode direct analysis in real time mass spectrometry – Proton/ammonium adduct selectivities of 600-sample in-house chemical library

Sugimura

Furuya

Yatsu

et al. 2017

Eur J Mass Spectrom (Chichester)

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In this study, direct analysis in real time adduct selectivities of a 558 in-house high-resolution mass spectrometry sample library was evaluated. The protonated molecular ion ([M + H]) was detected in 462 samples. The ammonium adduct ion ([M + NH]) was also detected in 262 samples. [M + H] and [M + NH] molecular ions were observed simultaneously in 166 samples. These adduct selectivities were related to the elemental compositions of the sample compounds. [M + NH] selectivity correlated with the number of oxygen atom(s), whereas [M + H] selectivity correlated with the number of nitrogen atom(s) in the elemental compositions. For compounds including a nitrogen atom and an oxygen atom [M + H] was detected; [M + NH] was detected for compounds including an oxygen atom only. Density functional theory calculations were performed for selected library samples and model compounds. Energy differences were observed between compounds detected as [M + H] and [M + NH], and between compounds including a nitrogen atom and an oxygen atom in their elemental compositions. The results suggested that the presence of oxygen atoms stabilizes [M + NH], but not every oxygen atom has enough energy for detection of [M + NH]. It was concluded that the nitrogen atom(s) and oxygen atom(s) in the elemental compositions play important roles in the adduct formation in direct analysis in real time mass spectrometry.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 94%

“…The calculation details are given in our previous studies. 15,17 Results and discussion Observed DART adducts for in-house chemical library…”

Section: Calculation Of Tpsamentioning

confidence: 99%

Section: Calculation Of Tpsamentioning

confidence: 99%

See 2 more Smart Citations

Observed adducts on positive mode direct analysis in real time mass spectrometry – Proton/ammonium adduct selectivities of 600-sample in-house chemical library

Sugimura

Furuya

Yatsu

et al. 2017

Eur J Mass Spectrom (Chichester)

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show abstract

“…Previously, we have used the topological polar surface area (tPSA) to report on the evaluation of the performance of mass spectrometer ion sources in terms of molecular polarity and molecular weight. 18 We have observed that tPSA can easily express molecular polarity using two-dimensional chemical structures without time-consuming quantum chemical calculations. 19 Furthermore, we found that tPSA satisfactorily expressed the polarity of the analytes in the ionization of mass spectrometry.…”

Section: Introductionmentioning

confidence: 99%

Prediction of Adducts on Positive Mode Electrospray Ionization Mass Spectrometry: Proton/Sodium Selectivity in Methanol Solutions

Sugimura

Furuya

Yatsu

et al. 2015

Eur J Mass Spectrom (Chichester)

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We used positive mode electrospray ionization (ESI) mass spectrometry to examine 540 in-house high-resolution mass spectrometry (HRMS) samples that formed an adducted positive ion. Of the 540 samples, the sodium adduct ([M+Na]⁺) was detected in 480 samples, and the protonated molecule ([M+H]⁺) was detected in 92 samples; both [M+Na]⁺ and [M+H]⁺ were detected in 32 samples. No other adduct ions were predominant. The selectivities of these adducts were evaluated by a two-dimensional plot using topological polar surface area (tPSA) and molecular weight. Two predominant trends were observed: [M+H]⁺ converged around tPSA (Å²) = 20 and molecular weight = 250, and the selectivity for [M+Na]⁺ correlated with the tPSA value. These observations were found to be related to the elemental composition of the sample compounds. From the results obtained by positive mode ESI mass spectroscopy under our experimental conditions, predominant trends were observed with respect to adduct selectivity: compounds containing oxygen atom(s) form [M+Na]⁺, and compounds containing nitrogen but not oxygen atom(s) form [M+H]². Based on these trends, we developed the "Nitrogen-Oxygen rule" (NO rule) to predict the adduct formed by a given compound on positive mode ESI. This NO rule provides a guideline to estimate elemental composition using ESI-HRMS with methanol as mobile phase.

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Ir‐Catalyzed Enantioselective Intra‐ and Intermolecular Formal C−H Conjugate Addition to β‐Substituted α,β‐Unsaturated Esters

et al. 2018

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An enantioselective intramolecular formal C−H conjugate addition of 4‐methyl 1‐aryl 2‐methylfumarates proceeded using a chiral iridium catalyst. A benzoylamide group served as a directing group, and chiral γ‐lactones with a quaternary all‐carbon stereogenic center were obtained with up to excellent ee. In the intermolecular reaction of N‐arylbenzamides with β‐substituted acrylates, C−H bond activation selectively occurred at the ortho‐position of carbonyl groups, and highly enantioselective formal C−H conjugate addition proceeded.

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Comparison of the Applicability of Mass Spectrometer Ion Sources Using a Polarity—Molecular Weight Scattergram with a 600-Sample In-House Chemical Library

Cited by 10 publications

References 21 publications

Observed adducts on positive mode direct analysis in real time mass spectrometry – Proton/ammonium adduct selectivities of 600-sample in-house chemical library

Observed adducts on positive mode direct analysis in real time mass spectrometry – Proton/ammonium adduct selectivities of 600-sample in-house chemical library

Prediction of Adducts on Positive Mode Electrospray Ionization Mass Spectrometry: Proton/Sodium Selectivity in Methanol Solutions

Ir‐Catalyzed Enantioselective Intra‐ and Intermolecular Formal C−H Conjugate Addition to β‐Substituted α,β‐Unsaturated Esters

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