Synthesis and characterization of a series of <i>N,N′</i>‐substituted urea derivatives by using electrospray ionization tandem mass spectrometry: Differentiation of positional isomers

Singh, Dilip Kumar; Chauthe, Siddheshwar Kisan; Anjanappa, Prakash; Kumar, Sumit; Arulraj, Ruba A.; Gajjela, Raju; Mohammed, V. Noor; Kanthappa, Venkatesh T.; Karmakar, Ananta; Gupta, Arun Kumar; Bajpai, Lakshmikant; Bagadi, Muralidhararao; Mathur, Arvind

doi:10.1002/rcm.9161

Cited by 2 publications

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“…However, these types of mass spectrometry are expensive and highly specific, making them difficult to popularize in ordinary laboratories. At present, most studies focus on the establishment of separation and analysis methods for isomeric pesticides, as well as the analysis of mass spectrometry cleavage pathways for a certain class of compounds 28–31 . Quantum chemical methods combined with collision‐induced dissociation (CID) on the mechanism of mass spectrometry separation and identification, as well as the effect of the mass spectrometry cleavage mechanism on different types of isomers, still account for a minority of studies 13…”

Section: Introductionmentioning

confidence: 99%

“…At present, most studies focus on the establishment of separation and analysis methods for isomeric pesticides, as well as the analysis of mass spectrometry cleavage pathways for a certain class of compounds. [28][29][30][31] Quantum chemical methods combined with collision-induced dissociation (CID) on the mechanism of mass spectrometry separation and identification, as well as the effect of the mass spectrometry cleavage mechanism on different types of isomers, still account for a minority of studies. 13 Radix Codonopsis, as a typical rhizome traditional Chinese medicine (TCM), has long been used to treat a variety of diseases containing bronchitis, cough, and allergic lung inflammation.…”

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confidence: 99%

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A computational and experimental study of cis–trans isomeric pesticides based on collision‐induced dissociation of high‐resolution mass spectrometry

Zhang,

Chang,

Chen

et al. 2024

Rapid Comm Mass Spectrometry

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RationalePesticide isomers are widely available in agricultural production and may vary widely in biological activity, potency, and toxicity. Chromatographic and mass spectrometric analysis of pesticide isomers is challenging due to structural similarities.MethodsBased on liquid chromatography time‐of‐flight mass spectrometry, identification of cis–trans isomeric pesticides was achieved through retention time, characteristic fragment ions, and relative abundance ratio. Furthermore, theoretical and basic research has been conducted on the differences in characteristic fragment ions and their relative abundance ratios of cis–trans isomers. On the one hand, the cleavage pathways of six cis–trans isomers were elucidated through collision‐induced dissociation to explain different fragment ions of the isomers. On the other hand, for those with the same fragment ions but different abundance ratios, energy‐resolved mass spectrometry combined with computational chemical density functional theory in terms of kinetics, thermodynamics, and bond lengths was employed to explain the reasons for the differences in characteristic fragment ions and their abundance ratios.ResultsA high‐resolution mass spectrometry method was developed for the separation and analysis of cis–trans isomers of pesticides in traditional Chinese medicine Radix Codonopsis, and six pesticide isomers were distinguished by retention time, product ions, and relative abundance ratios. The limits of quantification of the six pesticides were up to 10 μg/kg, and the linear ranges of them were 10–200 μg/kg, with coefficients of determination (R2) > 0.99, which demonstrated the good linearity of the six pesticides. The recoveries of the pesticides at spiked concentrations of 10, 20, and 100 μg/kg reached 70–120% with relative standard deviations ≤20%.ConclusionsIt was demonstrated that the application of the method was well suited for accurate qualitative and quantitative analysis for isomers with different structures, which could avoid false‐negative results caused by ignoring other isomers effectively.

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confidence: 99%

A computational and experimental study of cis–trans isomeric pesticides based on collision‐induced dissociation of high‐resolution mass spectrometry

Zhang,

Chang,

Chen

et al. 2024

Rapid Comm Mass Spectrometry

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Mass spectrometric‐based investigation of differentially protected azatryptophan derivatives using Orbitrap mass spectrometry: Differentiation of positional isomers under protonation and alkali‐cationization conditions

Gajjela

Kandula

Kuppusamy

et al. 2022

Rapid Comm Mass Spectrometry

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Rationale: Differentiation and structural characterization of positional isomers of differentially protected azatryptophan derivatives using electrospray ionization highresolution tandem mass spectrometry (ESI-HRMS/MS) is important from the perspective of drug discovery research. Also, these derivatives can be used as building blocks for the synthesis of various biologically active compounds and have attracted significant attention in the field of modern drug discovery, especially peptide-based drugs, protein folding and protein-protein interactions because of their interesting spectral properties. Methods: ESI-HRMS/MS in positive ionization mode was used to differentiate and characterize positional isomers of protected azatryptophan derivatives. Results: ESI-HRMS/MS of [M + H] + and [M + Na] + ions of positional isomers of differentially protected azatryptophan derivatives display distinct fragmentation patterns. The MS/MS of [M + H] + ion of isomer 1 showed an additional ion at m/z 358.0846 ([M + H-Boc-C 14 H 10 -HF] + ) which was not present for 4. The fragment ion at m/z 332.0857 was observed for 1 and not for 4 which would be formed by the expulsion of butyloxycarbonyl (Boc) and fluorenylmethyloxycarbonyl (Fmoc) groups. Moreover, the ions 422.0812 and 378.0912 are found to be relatively more abundant for isomer 4 which could be probably attributed to the formation of stable ions. Similarly, other positional isomers exhibited distinct fragmentation from one another. Conclusions: The present study demonstrates that ESI-HRMS/MS can be used for differentiation and structural characterization of positional isomers of protected azatryptophan derivatives. The MS/MS of [M + H] + and [M + Na] + ions of these positional isomers displayed differences in their fragmentation behaviour. The impact of different substitutions at different positions (1 and 6) of protected azatryptophan derivatives (1-6) on their fragmentation behaviour was also investigated in detail. Also, the nitrogen atom at different positions in the pyrrolopyridine ring led to different fragmentation patterns.

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Synthesis and characterization of a series of N,N′‐substituted urea derivatives by using electrospray ionization tandem mass spectrometry: Differentiation of positional isomers

Cited by 2 publications

References 20 publications

A computational and experimental study of cis–trans isomeric pesticides based on collision‐induced dissociation of high‐resolution mass spectrometry

A computational and experimental study of cis–trans isomeric pesticides based on collision‐induced dissociation of high‐resolution mass spectrometry

Mass spectrometric‐based investigation of differentially protected azatryptophan derivatives using Orbitrap mass spectrometry: Differentiation of positional isomers under protonation and alkali‐cationization conditions

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