Derivatization for electrospray ionization-mass spectrometry. 4. Alkenes and alkynes

Berkel, Gary J. Van; Quirke, J. Martin E.; Adams, Christopher L.

doi:10.1002/(sici)1097-0231(20000530)14:10<849::aid-rcm954>3.0.co;2-t

Cited by 47 publications

(41 citation statements)

References 41 publications

(60 reference statements)

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“…Then, the inherent electrochemical aspect of electrospray [6][7][8] has opened the way to the study of electrochemically induced reactions [9][10][11][12] like rearrangements of biological molecules. [13][14][15] Moreover, electro-active probes have been developed to chemically derivatize weakly ionisable compounds, [16][17][18][19][20][21] and to label specific amino acids. 22 Recently, we have developed a polymer micro-ESI emitter comprised of a microband electrode.…”

Section: Introductionmentioning

confidence: 99%

Probing Cysteine Reactivity in Proteins by Mass Spectrometric EC-Tagging

2006

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The on-line electrochemical tagging (EC-tagging) of cysteine residues in proteins during mass spectrometry is studied to probe the cysteine environment. Benzoquinone probes electrogenerated at a microspray electrode react with the thiol functions of the proteins within a microchannel and the products are analyzed by mass spectrometry. The fundamentals of the technique are discussed, with a focus on the kinetic aspects. The EC-tagging efficiency of the cysteine residues in proteins is used to probe their environment. Experiments with unmodified proteins and their chemically reduced forms highlight the strong effect of the cysteine site reactivity on the tagging efficiencies. This study highlights relevant parameters for such on-line electrochemical derivatization/MS detection strategies.

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Section: Introductionmentioning

confidence: 99%

Probing Cysteine Reactivity in Proteins by Mass Spectrometric EC-Tagging

2006

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“…Since then, Van Berkel's group and others have comprehensively investigated the theoretical aspects of electrochemistry in electrospray [31][32][33][34][35][36][37][38][39][40][41][42] as well as made significant advances in electrochemical flow cell hyphenation with electrospray mass spectrometry (ESI-MS) [37,[43][44][45][46], and electrochemical derivatization strategies for analyte detection by ESI-MS [47][48][49][50][51]. Moreover, Bruins and coworkers have used EC-ESI-MS to study or mimic biologically relevant electrochemical reactions [52], such as phase I oxidative reactions in drug metabolism [53] or cytochrome P450 catalyzed reactions [54].…”

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confidence: 99%

Generation of mass tags by the inherent electrochemistry of electrospray for protein mass spectrometry

Roussel

Dayon

Lion

et al. 2004

J. Am. Soc. Mass Spectrom.

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We present herein a review of our work on the on-line electrochemical generation of mass tags toward cysteine residues in peptides and proteins. Taking advantage of the inherent electrochemical nature of electrospray generated from a microfabricated microspray emitter, selective probes for cysteine were developed and tested for on-line nonquantitative mass tagging of peptides and proteins. The nonquantitative aspect of the covalent tagging thus allows direct counting of free cysteines in the mass spectrum of a biomolecule through additional adduct peaks. Several substituted hydroquinones were investigated in terms of electrochemical properties, and their usefulness for on-line mass tagging during microspray experiments were assessed with L-cysteine, peptides, and intact proteins. Complementarily, numerical simulations were performed to properly understand the respective roles of mass transport, kinetics of electrochemical-chemical reactions, and design of the microspray emitter in the mass tagging overall efficiency. Finally, the on-line electrochemical tagging of cysteine residues was applied to the analysis of tryptic peptides of purified model proteins for protein identification through peptide mass fingerprinting. (J Am Soc Mass Spectrom 2004, 15, 1767-1779

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“…Neutral mono-and disaccharides could be oxidized as their cyclic ferrocenyl boronic esters and analyzed by MS-MS and MS-MS-MS [48]. Ferrocenecarboxylic acids [49] were used for derivatization and even alkenes could be ionized with electrochemical oxidation by derivatization with an electroactive group like ferrocene boronic acid [50,51]. Additional electrochemical cells were coupled to electrospray to provide a specific oxidation or reduction potential.…”

Section: Electrochemistrymentioning

confidence: 99%

LC-MS analysis in the aquatic environment and in water treatment ? a critical review

Zwiener

Frimmel

2004

Analytical and Bioanalytical Chemistry

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LC-MS has become an invaluable technique for trace analysis of polar compounds in aqueous samples of the environment and in water treatment. LC-MS is of particular importance due to the impetus it has provided for research into the occurrence and fate of polar contaminants, and of their even more polar transformation products. Mass spectrometric detection and identification is most widely used in combination with sample preconcentration, chromatographic separation and atmospheric pressure ionization (API). The focus of the first part of this review is directed particularly toward instruments and method development with respect to their applications for detecting emerging contaminants, microorganisms and humic substances (HS). The current status and future perspectives of 1) mass analyzers, 2) ionization techniques to interface liquid chromatography (LC) with mass spectrometry (MS), 3) methods for preconcentration and separation with respect to their application for water analysis are discussed and examples of applications are given. Quadrupole and ion trap mass analyzers with electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI) are already applied in routine analysis. Time-of-flight (TOF) mass spectrometers are of particular interest for accurate mass measurements for identification of unknowns. For non-polar compounds, different ionization approaches have been described, such as atmospheric pressure photoionization (APPI), electrochemistry with ESI, or electron capture ionization with APCI. In sample preconcentration and separation, solid phase extraction (SPE) with different non-selective sorbent materials and HPLC on reversed-phase materials (RP-HPLC) play the dominant role. In addition, various on-line and miniaturized approaches for sample extraction and sample introduction into the MS have been used. Ion chromatography (IC), size-exclusion chromatography (SEC), and capillary electrophoresis (CE) are alternative separation techniques. Furthermore, the issues of compound identification, matrix effects on quantitation, development of mass spectral libraries and the topic of connecting analysis and toxicity bioassays are addressed.

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Derivatization for electrospray ionization-mass spectrometry. 4. Alkenes and alkynes

Cited by 47 publications

References 41 publications

Probing Cysteine Reactivity in Proteins by Mass Spectrometric EC-Tagging

Probing Cysteine Reactivity in Proteins by Mass Spectrometric EC-Tagging

Generation of mass tags by the inherent electrochemistry of electrospray for protein mass spectrometry

LC-MS analysis in the aquatic environment and in water treatment ? a critical review

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