Selective Analysis of Sulfur-Containing Species in a Heavy Crude Oil by Deuterium Labeling Reactions and Ultrahigh Resolution Mass Spectrometry

Xu-xiao, Wang; Schräder, Wolfgang

doi:10.3390/ijms161226205

Cited by 22 publications

(15 citation statements)

References 31 publications

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“…The mixture was stirred at 25 °C for 6 h in the dark, and the solution was then lyophilized to obtain the product. Fourier transform ion cyclotron resonance MS (solarix, Bruker Daltonics, Bremen, Germany) using electrospray ionization was used to verify the precise molecular mass of the compound [44]. Mass spectrometry coupled with HPLC (1260, Agilent, Santa Clara, CA, USA) was used to develop a method for its quantitative analysis.…”

Section: Methodsmentioning

confidence: 99%

2-Deoxyglucose-Modified Folate Derivative: Self-Assembling Nanoparticle Able to Load Cisplatin

Jin

Wang

et al. 2019

Molecules

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Folic acid has been widely introduced into nano-drug delivery systems to give nanoparticle-targeted characteristics. However, the poor water solubility of folic acid may hinder the exploitation of its ability to load antineoplastic drugs. In the present study, we designed a new folate derivative (FA-2-DG) synthesized from folic acid and 2-Deoxyglucose (2-DG). The aim of this study was to evaluate the self-assembly characteristics of FA-2-DG, and its ability of loading cisplatin. The critical micelle concentration was 7.94 × 10−6 mol L−1. Fourier transform infrared spectroscopy indicated that hydrogen bonding interaction is a main driving force for the self–assembly of FA-2-DG. The particle was stable in pure water or 0.5% bovine serum albumin dispersions. By forming a coordination bond, the particles assembled from FA-2-DG can load cisplatin. The loading efficiency was maximal when the molar ratio of FA-2-DG to cisplatin was 2:1.

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Section: Methodsmentioning

confidence: 99%

2-Deoxyglucose-Modified Folate Derivative: Self-Assembling Nanoparticle Able to Load Cisplatin

Jin

Wang

et al. 2019

Molecules

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“…Wang et al introduced the deuterium labeling technique to achieve characterization of sulfur‐containing species in crude oil . The heavy crude oil was treated with deuterated alkylating reagents and then analyzed by ESI MS.…”

Section: Use Of the In‐apci/appi Source Isotope Exchangementioning

confidence: 99%

“…[339][340][341][342] Wang et al introduced the deuterium labeling technique to achieve characterization of sulfur-containing species in crude oil. 343 The heavy crude oil was treated with deuterated alkylating reagents and then analyzed by ESI MS. Here only sulfur-containing compounds were alkylated by employing deuterium labeled alkylating reagents to selectively differentiate the tagged sulfur species from the original crude oil.…”

Section: Speciation Of S Containing Compounds In Crude Oilsmentioning

confidence: 99%

Hydrogen/deuterium exchange in mass spectrometry

Kostyukevich

Acter

Zherebker

et al. 2018

Mass Spectrometry Reviews

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The isotopic exchange approach is in use since the first observation of such reactions in 1933 by Lewis. This approach allows the investigation of the pathways of chemical and biochemical reactions, determination of structure, composition, and conformation of molecules. Mass spectrometry has now become one of the most important analytical tools for the monitoring of the isotopic exchange reactions. Investigation of conformational dynamics of proteins, quantitative measurements, obtaining chemical, and structural information about individual compounds of the complex natural mixtures are mainly based on the use of isotope exchange in combination with high resolution mass spectrometry. The most important reaction is the Hydrogen/Deuterium exchange, which is mainly performed in the solution. Recently we have developed the approach allowing performing of the Hydrogen/Deuterium reaction on-line directly in the ionization source under atmospheric pressure. Such approach simplifies the sample preparation and can accelerate the exchange reaction so that certain hydrogens that are considered as non-labile will also participate in the exchange. The use of in-ionization source H/D exchange in modern mass spectrometry for structural elucidation of molecules serves as the basic theme in this review. We will focus on the mechanisms of the isotopic exchange reactions and on the application of in-ESI, in-APCI, and in-APPI source Hydrogen/Deuterium exchange for the investigation of petroleum, natural organic matter, oligosaccharides, and proteins including protein-protein complexes. The simple scenario for adaptation of H/D exchange reactions into mass spectrometric method is also highlighted along with a couple of examples collected from previous studies.

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“…8 For the ionization techniques, the most common has been, by far, electrospray ionization (ESI). [9][10][11][12] ESI FT-ICR MS has, therefore, been widely used to determine sulfurcontaining species in heavy crude oil 13 and non-polar polyaromatic hydrocarbons and polyaromatic heterocycles in asphaltenes, 10,14 as well as to classify biodegraded and non-biodegraded crude oils focused on the O 2 -class. 12 Atmospheric pressure photoionization (APPI) has also been applied to crude oil analysis, [15][16][17] but much less intensively, most particularly when the goal is to efficiently ionize nonpolar sulfur species and polycyclic aromatic hydrocarbons, which are interesting classes because they affect the petroleum refinery and its regulation by governmental agencies.…”

Section: Introductionmentioning

confidence: 99%

Optimization of Atmospheric Pressure Photoionization for the Crude Oil Analysis Using Ultra-High Resolution Mass Spectrometry

Santos

Pudenzi

Wisniewski

et al. 2018

J. Braz. Chem. Soc.

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Design of experiments (DOE) applied to mass spectrometry (MS), mainly focusing on the optimization of ionization techniques, has been applied to optimize experiments in order to provide the highest amount of information with the lowest number of experiments. However, DOE has not been used in petroleomics. For the first time, we applied DOE to optimize the main parameters associated with the crude oil analysis in a petroleomics approach. For the ionization technique, atmospheric pressure photoionization (APPI) has been selected and data were acquired in a high resolution (400,000 at m/z 400) and high mass accuracy (< 1 ppm) Fourier transform ion cyclotron resonance (FT-ICR) MS. Full and fractional two-level factorial designs were applied for the APPI(±) FT-ICR MS data set from two different crude oil samples with distinct physical and chemical characteristics. The standard ionization parameters that affect the MS responses of the crude oil analysis were optimized for both APPI(+)-MS and APPI(-)-MS. Such ionization parameters were then successfully applied to a crude oil and its saturated, aromatics, resin and asphaltene fractions, all with superior features of merit. Thus, the optimized APPI(±)-MS parameters should serve as reference and can be used as a guide for new studies in petroleomics.

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Selective Analysis of Sulfur-Containing Species in a Heavy Crude Oil by Deuterium Labeling Reactions and Ultrahigh Resolution Mass Spectrometry

Cited by 22 publications

References 31 publications

2-Deoxyglucose-Modified Folate Derivative: Self-Assembling Nanoparticle Able to Load Cisplatin

2-Deoxyglucose-Modified Folate Derivative: Self-Assembling Nanoparticle Able to Load Cisplatin

Hydrogen/deuterium exchange in mass spectrometry

Optimization of Atmospheric Pressure Photoionization for the Crude Oil Analysis Using Ultra-High Resolution Mass Spectrometry

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