Selective Detection of Derivatized Alcohols and Phenols in Essential Oils by Electrospray-Tandem Mass Spectrometry

Quirke, J. Martin E.; Hsu, Yu‐Chin; Berkel, Gary J. Van

doi:10.1080/10412905.2001.9712224

Cited by 7 publications

(4 citation statements)

References 16 publications

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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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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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“…[ 25 , 26 ]. Among them, FluMP can react with primary and secondary alcohols and phenols in complex mixtures [ 27 , 28 ]. After derivatization, a quaternary ammonium salt was introduced to the target estrogens, thus greatly improveing the response in mass spectrometry.…”

Section: Resultsmentioning

confidence: 99%

Rapid Detection of Estrogens in Cosmetics by Chemical Derivatization and Paper-Spray Ionization Mass-Spectrometry

et al. 2023

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Estrogens in personal care products are harmful to customers. Conventional methods such as HPLC and LC-MS require tedious sample pretreatment and long analytical time. Paper-spray ionization mass spectrometry (PSI-MS) is a powerful tool for the determination of compounds with little time and minimal pretreatment procedures. Since most estrogens show poor responses in PSI-MS, we developed a chemical derivatization and PSI-MS method to determinate three estrogens: estradiol, estriol and ethinyloestradiol with estradiol valerate as the internal standard (I.S.). After derivatization with 2-fluoro-1-methyl-pyridinium-p-toluene-sulfonate, the three estrogens could be quantified in seconds. This method showed good linearity in the range of 0.1~30 μg·mL−1, with R2 > 0.999. Their recovery results were all between 85%~115%. The limits of detection (LOD) were 0.04 μg·mL−1, 0.02 μg·mL−1 and 0.02 μg·mL−1 for estradiol, estriol and ethinyloestradiol respectively, which improved around 200, 2000, and 900 times compared to non-derivative PSI-MS. The method could quantitatively determine estrogens in cosmetics.

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“…Thus, to verify whether these ketones also contain a phenol OH group, the heating oil (stored for 18 months) and the diesel sample after HDS (145 ppm of S) were derivatized with 2-fluoro-1-methylpyridinium p-toluenesulfonate (TOS – ), FMP, as the derivatization reagent. This reagent has been used for a selective derivatization of alcohols and phenols in essential oils . It is well-known that phenols can be analyzed by using the negative mode of ESI-MS, but it would be less useful for the phenols C n H x O 2 since ions from carboxylic acids of the same formula also present would be recorded as well and thus no selective information on the functionality would be gained.…”

Section: Resultsmentioning

confidence: 99%

Effect of Storage and Hydrodesulfurization on the Ketones in Fossil Fuels

Alhassan

Andersson

2015

Energy Fuels

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Stability of fuels on storage is a topic of major concern. Oxidation prone compounds are known to react with air oxygen to form polar oxygenated products that ultimately can precipitate as a gum. Ketones are such reactive compounds, and here they are analyzed in several materials. They are recorded in a diesel as a function of the degree of hydrodesulfurization (HDS). A ketone selective reagent is used to derivatize only ketones, thus avoiding confusion with other one oxygen-atom containing compounds. The analysis was done using ultrahigh resolution Orbitrap mass spectrometry. The alkanones that were present in the original material are removed through HDS. Plenty of mainly aromatic ketones are formed when the fuel is stored in contact with air. A heating oil was stored under near-ambient conditions and analyzed after 12 and 18 months. Aromatic ketones arose throughout the storage, but their pattern did not change with time. A phenol selective derivatization reagent was used to show that many ketones containing a total of two oxygen atoms are in fact hydroxyphenyl alkyl ketones. A sediment contained ketones possessing a total of one to five oxygen atoms. The advantage of using selective derivatization reagents to differentiate between isomers based on their functional groups is demonstrated.

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Selective Detection of Derivatized Alcohols and Phenols in Essential Oils by Electrospray-Tandem Mass Spectrometry

Cited by 7 publications

References 16 publications

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

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

Rapid Detection of Estrogens in Cosmetics by Chemical Derivatization and Paper-Spray Ionization Mass-Spectrometry

Effect of Storage and Hydrodesulfurization on the Ketones in Fossil Fuels

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