Characterization of organic dyes aided by hydrogen-deuterium exchange in liquid secondary ion mass spectrometry (liquid SIMS)

Bentz, B. L.; Gale, Peggy

doi:10.1016/0168-1176(87)87045-3

Cited by 23 publications

(9 citation statements)

References 25 publications

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“…The FAB mass spectra of the compounds were obtained using two matrices that are known to provide different levels of the reduction under FAB/SIMS: glycerol, the most popular FAB matrix, in which the reduction effect was observed in many works,19–22, 27, 33, 34 and NBA, which possesses oxidative properties and thus hampers the reduction 27, 36, 37…”

Section: Resultsmentioning

confidence: 99%

“…Since a lot of previous studies in the early days of FAB have concerned the reduction process of various organic and inorganic compounds under particle bombardment conditions,1–4, 16–37 our first task was to summarize the available literature information. In this, we focused our attention mainly on aromatic heterocyclic compounds bearing structural similarity with the systems investigated in the present work.…”

Section: Introductionmentioning

confidence: 99%

“…To evaluate different aspects of the mechanisms of the redox processes under FAB/SIMS, several model experiments with different variations of the analytes and matrix solvents were performed 19–31. Although the chemical inertness is one of the requirements for matrix solvent compounds, some of them can possess either oxidative or reductive properties; e.g.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of the reduction of imidazophenazine dye derivatives under fast‐atom‐bombardment mass‐spectrometric conditions

et al. 2005

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Satellite [M + 2](+*) and [M + 3](+) peaks accompanying the common peak of the protonated molecule [M + H](+) that are known to indicate the occurrence of a reduction process were observed in the fast atom bombardment (FAB) mass spectra of imidazophenazine dye derivatives in glycerol matrix. The distribution of the abundances in the [M + nH](+) peak group varied noticeably for different derivatives. This indicated different levels of the reduction depending on the different structure variations of the studied molecules. In the search for correlations between the mass spectral pattern and the structural features of the dyes, ab initio HF/6-31++G** quantum chemical calculations were performed. They revealed that the abundances of the [M + 2](+*) and [M + 3](+) ions show growth proportional to the decrease of the energy of the lowest unoccupied molecular orbital, i.e. proportional to the increase of the electron affinity of the dye molecule. A method for rapid screening of reductive properties of sets of dye derivatives on the basis of the FAB mass spectral data is discussed.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Evaluation of the reduction of imidazophenazine dye derivatives under fast‐atom‐bombardment mass‐spectrometric conditions

et al. 2005

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“…HPLC separation of dipeptides 5-20 was performed using a Waters YMC ODS AM column (4.6 ϫ 250 mm, 5 mm) and a standard linear gradient over 40 min starting from 95%/5%/0.1% to 5%/95%/0.1% water/acetonitrile/TFA at a flow rate of 1 mL/min at ambient temperature. The deuterium exchange experiments were performed using identical conditions replacing water and TFA with deuterium oxide and d-TFA, respectively,°as°has°previously°been°described° [7].…”

Section: Methodsmentioning

confidence: 99%

“…The coupling of HPLC and mass spectrometry combines a powerful separation technique with the sensitive and informative MS detection mode, which opens a new venue for H/D exchange MS analysis of complex mixtures containing polar compounds. To date, various MS techniques including chemical ionization detection mass spectrometry (CI/MS) [5], fast atom bombardment mass spectrometry (FAB/MS) [6], liquid secondary ion mass spectrometry (LSI/MS) [7], electrospray mass spectrometry (ESI/MS) [8], and thermospray mass spectrometry (TSP/MS) [9] utilizing a deuterated mobile phase or matrix have been reported. Deuterated mobile phase HPLC has also successfully been combined with NMR [10] and IR spectroscopy [11].…”

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confidence: 99%

Elucidation of the presence and location of t-Boc protecting groups in amines and dipeptides using on-column H/D exchange HPLC/ESI/MS

Wolf

Villalobos

Cummings

et al. 2005

J. Am. Soc. Mass Spectrom.

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High performance liquid chromatography/mass spectrometry (HPLC/MS) has become a widely used technique for routine analysis of pharmaceutical compounds. The constant search for new drugs requires the development of time-efficient methods that can be employed in high-throughput screening of combinatorial libraries of a variety of compounds, including amines and peptides. Conventional HPLC/MS is a powerful technique that can easily be automated and is suitable for comprehensive screening purposes. However, the unequivocal determination of the presence and location of important carbamoyl protecting groups of amines is often elusive because of their inherent instability under MS conditions. In this study, the use of on-column H/D exchange HPLC/ESI/MS for structure elucidation of t-Boc protecting groups which can often not be detected by MS because of facile McLafferty rearrangement has been examined. We demonstrate that employing a deuterated mobile phase in HPLC/MS analysis provides a convenient tool for the determination of the absence or presence of t-Boc protecting groups in amines and peptides. . This fragmentation pathway may proceed via a labile intermediate carbamoyl acid intermediate 3, which easily eliminates carbon dioxide and is therefore often not observed. Because the unprotected amino alcohol 4 affords fragment 2 after ionization in the MS detector, mass spectrometry does not provide a means to differentiate between 1 and 4, i.e., the determination of the presence of the t-Boc group requires isolation and further spectroscopic analysis or the use of reference samples for a time-consuming comparison of HPLC retention times which is unsuitable for high-throughput screening.Structure elucidation by mass spectrometry has become increasingly successful through the introduction of chemical ionization with ND 3 , D 2 O, and CD 3 OD for exchange of hydrogen for deuterium of organic compounds in the gas phase [2]. This technique can be applied to H/D exchange MS analysis of various classes of compounds including alcohols, carboxylic acids, amines, amides, and thiols [3]. It has also been shown that hydrogens bonded to carbon atoms in aromatic compounds can be replaced by deuterium in the gas phase [4]. The coupling of HPLC and mass spectrometry combines a powerful separation technique with the sensitive and informative MS detection mode, which opens a new venue for H/D exchange MS analysis of complex mixtures containing polar compounds. To date, various MS techniques including chemical ionization detection mass spectrometry (CI/MS) [5], fast atom

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Mass spectrometry of domoic acid, a marine neurotoxin

Thibault¹,

Quilliam²,

Jamieson³

et al. 1989

Biol. Mass Spectrom.

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Domoic acid is a naturally occurring amino acid, formerly available in iimited amounts as a natural product of some algae of the family Rhodomelaceae. As the result of a recent incidence of toxicity in cultured blue mussels (Mytiius eáulis) from a highly localized region of Atlantic Canada, useful amounts of t h i substance are likely to become available in the near future. Domoic acid is an important substance for fundamental studies in neurobiology as it possesses the highest afinity amongst known substances for the kainate receptors of the central nervous system. The present work describes fast atom bombardment (FAB) m a s spectra of domoic acid, and of some of its isomers present in minor quantities in contaminated mussel extracts. These FAB spectra are subject to interferences from beam-induced reduction reactions associated with matrices such as glycerol, but not with others such as 3-nitrobenzyl alcohol. Tandem mass spectrometry of the MH+ ions from these compounds is also reported. As a more feasible approach to quantitative analysis at trace levels, formation of the volatile tert-butyldimethylsilyl derivatives has been investigated and shown to be highly promising.

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Characterization of organic dyes aided by hydrogen-deuterium exchange in liquid secondary ion mass spectrometry (liquid SIMS)

Cited by 23 publications

References 25 publications

Evaluation of the reduction of imidazophenazine dye derivatives under fast‐atom‐bombardment mass‐spectrometric conditions

Evaluation of the reduction of imidazophenazine dye derivatives under fast‐atom‐bombardment mass‐spectrometric conditions

Elucidation of the presence and location of t-Boc protecting groups in amines and dipeptides using on-column H/D exchange HPLC/ESI/MS

Mass spectrometry of domoic acid, a marine neurotoxin

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