Analysis of anionic surfactants by mass spectrometry/mass spectrometry with fast atom bombardment

Lyon, P. A.; Stebbings, William L.; Crow, Frank W.; Tomer, Kenneth B.; Lippstreu, Dixie L.; Gross, Michael L.

doi:10.1021/ac00265a004

Cited by 104 publications

(49 citation statements)

References 33 publications

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“…The process was first extensively studied with unsaturated fatty acids and their derivatives by Gross et al [21]. Other examples include anionic surfactants containing a sulfate polar head group [22] as well as more rigid steroid conjugates containing a sulfate group on the peripheral ring, with predominant fragmentation occurring at a distal reaction site [23]. Interestingly, there are not many examples of collision induced dissociation of carbohydrate ions, where charge-remote fragmentation mechanisms have been implicated.…”

Section: Labeling Studies and Mechanisms Of 02 A 2 And 02 X 1 Ion Fmentioning

confidence: 99%

Delineating mechanisms of dissociation for isomeric heparin disaccharides using isotope labeling and ion trap tandem mass spectrometry

Saad

Leary

2004

J. Am. Soc. Mass Spectrom.

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Heparin and heparan sulfate (HS) glycosaminoglycans have been identified as important players in many physiological as well as pathophysiological settings. A better understanding of the biosynthesis and structure of these molecules is critical for further elucidation of their biological function. We have demonstrated the successful use of negative electrospray ionization tandem mass spectrometry in the differentiation of all twelve standard heparinbuilding blocks, including the potentially important N-unsubstituted disaccharides. Collision induced dissociation of each of the isomeric disaccharides provided unique product ion spectra, useful for identification and quantification of the relative amounts of each isomer present. In the research presented herein, isotopic labeling studies using 18 O and 2 H were used to determine the origins of each of the neutral losses observed in the product ion spectra, and mechanisms of dissociation consistent with the observed data were postulated. The general mechanisms postulated were for the generation of B, Y, and Z ions formed from glycosidic cleavages, as well as A and X ions formed from cross-ring cleavages. The eight isomeric heparin disaccharides all underwent cross-ring cleavage to form 0,2 X 1 and 0,2 A 2 ions, and further experiments suggest that the mechanisms of formation of these ions are through a charge-remote process. The tandem mass spectrometry data presented herein also provide a foundation for further developments towards a practical analysis tool for the structural elucidation of larger, biologically important heparin/HS oligosaccharides by using mass spectrometry. H eparin and heparan sulfate (HS) glycosaminoglycans (GAGs) have been implicated in a host of biological functions including blood coagulation, inflammatory processes, cell-cell and cellmatrix interactions, as well as cell growth and differentiation [1]. Although heparin has been used clinically as an anticoagulant for decades, and the closely related species, heparan sulfate has been identified as a key player with many biological roles, the absolute structures responsible for the various attributed functions are complex and have only recently been deciphered in a few specific cases. To better understand their biological roles in physiological as well as pathophysiological settings, it is necessary to gain a better understanding about the structure of heparin/HS at the molecular level.Heparin/HS polysaccharides consist of a repeating disaccharide unit of [HexA␤(1,4)GlcN␣(1,4)] n . The hexuronic acid (HexA) residue can be either L-iduronic acid (IdoA) or D-glucuronic acid (GlcA) depending on the stereochemistry of the C5 carboxylic acid group, and may be sulfated at the C2 position. In addition, the glucosamine units may be N-acetylated (GlcNAc), Nsulfated (GlcNS) or N-unsubstituted (GlcN), and can be further differentially sulfated at the C3 and C6 positions. Structural studies of heparin and HS have indicated differences between the two, such as the predominance of the trisulfated disaccharid...

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Section: Labeling Studies and Mechanisms Of 02 A 2 And 02 X 1 Ion Fmentioning

confidence: 99%

Delineating mechanisms of dissociation for isomeric heparin disaccharides using isotope labeling and ion trap tandem mass spectrometry

Saad

Leary

2004

J. Am. Soc. Mass Spectrom.

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“…Their procedure described in the following lines. The thickness of ethoxy number distribution as seen by Fast Atom Bombardthe oxide layer (either SiO 2 or TiO 2 ) was determined in air ment mass spectrometry (22,23) is close to that of nonionic or solvent by the four-zone method which cancels most of surfactants in the case of NPE4S and NPE10S, but much optical imperfections of both apparatus and cell windows more flattened in the case of NPE25S (24). Due to their (33).…”

Section: Npe4s 4 330mentioning

confidence: 99%

Adsorption of Polydisperse Surfactants on Solid Surfaces: An Ellipsometric Study

Luciani

Denoyel

1997

Journal of Colloid and Interface Science

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“…e loss of C n H 2n+2 is typical fragmentation in anionic surfactants. 12) In Japan, linear alkyl benzenesulfonate (LAS) is a leading detergent with an annual manufactured and imported quantity of 48,160 t in FY 2013. 13) Its monoisotopic masses of anionic forms are 297.1530 (4-decan-x-ylbenzenesulfonate, x=2-5, C 10 LAS), 311.1686 (4-undecan-x-ylbenzenesulfonate, x=2-6, C 11 LAS), 325.1843 (4-dodecan-x-ylbenzenesulfonate, x=2-6, C 12 LAS), and 339.1999 (4-tridecan-x-ylbenzenesulfonate, x=2-7, C 13 LAS).…”

Section: Resultsmentioning

confidence: 99%

Identification of Anthropogenic Compounds in Urban Environments and Evaluation of Automated Methods for Reading Fragmentation

et al. 2016

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A work ow based on liquid chromatography/high-resolution mass spectrometry (LC/HR-MS) was applied for the identi cation of compounds in urban environments. Substances extracted by solid-phase extraction from river water were wholly analyzed by LC/HR-MS without any puri cation. Fragmentation in collision-induced dissociation was manually studied for the 20 most intense ions in positive-and negativeion electrospray ionization with accurate mass determination at a resolution of 100,000. Sixteen anthropogenic compounds in the extract were identi ed and con rmed using standard reference reagents. ese compounds consisted of pharmaceuticals, surfactants, ame retardants, and industrial intermediates. e majority of the compounds are common in our daily life. In the identi cation process, two automated methods, MAGMa and MetFrag/MetFusion, for reading fragmentation were evaluated for the sixteen compounds. Although automated methods could be used to retrieve the correct molecular structures in most cases, they could not always be promoted to the top rank. Automated methods have yet to be a complete solution for identifying chemical compounds, but will considerably reduce the burden for humans in reading fragmentation.

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Analysis of anionic surfactants by mass spectrometry/mass spectrometry with fast atom bombardment

Cited by 104 publications

References 33 publications

Delineating mechanisms of dissociation for isomeric heparin disaccharides using isotope labeling and ion trap tandem mass spectrometry

Delineating mechanisms of dissociation for isomeric heparin disaccharides using isotope labeling and ion trap tandem mass spectrometry

Adsorption of Polydisperse Surfactants on Solid Surfaces: An Ellipsometric Study

Identification of Anthropogenic Compounds in Urban Environments and Evaluation of Automated Methods for Reading Fragmentation

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