Fast atom bombardment and collisional activation mass spectrometry as probes for the identification of positional isomers in a series of benzylated guanosines

Tondeur, Yves; Moschel, Robert C.; Dipple, Anthony; Koepke, Steven R.

doi:10.1021/ac00298a011

Cited by 18 publications

(3 citation statements)

References 44 publications

(35 reference statements)

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“…Therefore, this compound was assigned to p-hydroxybenzyl guanosine and the possible conjugated position is N 2 , by referring to the analogous result in literature (see Fig. 1 for structure) [28]. Similarly, peak 19 was assigned to p-hydroxybenzyl adenosine and the likely structure was N 6 -substituted (see Fig.…”

Section: Identification Of Phenolics and Nucleoside Derivatives In Gmentioning

confidence: 63%

Identification of phenolics and nucleoside derivatives in Gastrodia elata by HPLC‐UV‐MS

Wang

Xiao²,

Liang

et al. 2007

J of Separation Science

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An HPLC-UV-MS method for simultaneous identification of predominant phenolics and minor nucleoside derivatives in Gastrodia elata was developed, which was based on their UV and MS characteristics summarized through a series of homemade reference standard experiments. Phenolics showed characteristic UV lambda(max) at 267 nm, [M + NH(4)](+) base peak in positive mode and [M-H](-) base peak in negative mode while nucleosides exhibited UV lambda(max) at 255 nm, [M + H](+), [M-H + 2H(2)O](-) or [M-H + CH(3)COOH](-). Phenolics conjugates mainly underwent the consecutive loss of gastrodin residue (-268 U) and the combined loss of H(2)O and CO(2 )from the citric acid unit under negative MS/MS conditions whereas nucleosides simply lost the ribose (-132 U) under positive MS/MS conditions. According to these characteristics, a special pattern under MS/MS conditions and reported compound data for G. elata in the literature, not only 15 phenolics were identified but also 6 nucleoside derivatives were identified. Among these compounds, seven phenolics and three nucleoside derivatives have not been reported yet from G. elata.

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Section: Identification Of Phenolics and Nucleoside Derivatives In Gmentioning

confidence: 63%

Identification of phenolics and nucleoside derivatives in Gastrodia elata by HPLC‐UV‐MS

Wang

Xiao²,

Liang

et al. 2007

J of Separation Science

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“…While a variety of mass spectrometric techniques have been employed for the characterization of nucleic acid adducts (7), it has been fast atom bombardment (FAB) ionization, combined with tandem mass spectrometric methods, which has been used most widely for structural characterization of intact polycyclic aromatic hydrocarbons (PAH)-deoxynucleoside adducts and similar compounds (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). In studies where high-sensitivity static FAB characterization has been emphasized, chemical derivatization of isolated materials has typically been employed (10,11).…”

Section: Introductionmentioning

confidence: 99%

Application of capillary liquid chromatography coupled with tandem mass spectrometric methods to the rapid screening of adducts formed by the reaction of N-acetoxy-N-acetyl-2-aminofluorene with calf DNA

Wolf

Vouros²

1994

Chem. Res. Toxicol.

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Capillary liquid chromatography-continuous-flow fast atom bombardment mass spectrometry is applied to the detection of deoxynucleoside adducts of N-acetoxy-N-acetyl-2-aminofluorene. In such a configuration, normal scan and tandem mass spectrometric techniques are shown to provide useful structural information for an N-acetyl-N-(deoxyguanosin-8-yl)-2-aminofluorene adduct standard for low- nanogram (low-picomole) amounts sampled. In addition, multiple reaction monitoring gives limits of detection below 25 pg (50 fmol) for this adduct, suggesting the potential for routine screening of intact deoxynucleoside adducts formed below the 1:10(6) level from as little as 1 mg of DNA. When applied to the analysis of the products of an in vitro reaction of calf thymus DNA with N-acetoxy-N-acetyl-2-aminofluorene, these techniques are readily able to detect and supply structural data for the N2 and C8 deoxyguanosine adducts formed.

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“…The techniques normally employed to characterize these species at physiologically significant levels, including 32P-postlabeling [1,2], immunoassay [3,4], and fluorescence spectroscopy [5,61, are generally not able to provide pertinent structural information for identification of unknowns. Although the application of mass spectrometry to the structural analysis and detection of polyaromatic hydrocarbon (PAH)-DNA adducts has been somewhat limited, notable contributions to this field of study have been made by a number of groups [7][8][9][10][11][12][13][14][15][16][17][18]. However, except in a few cases [12-141, little attempt has been made to develop mass spectrometric techniques for the characterization of nanogram or lower amounts of the intact PAH adducts.…”

mentioning

confidence: 99%

Identification of deoxynucleoside—polyaromatic hydrocarbon adducts by capillary zone electrophoresis—Continuous Flow-fast atom bombardment mass spectrometry

Wolf

Vouros

Norwood

et al. 1992

J. Am. Soc. Mass Spectrom.

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Capillary zone electrophoresis coupled to continuous flow-fast atom bombardment mass spectrometry is shown to have utility for the detection and characterization of adducts formed by the covalent attachment of four polyaromatic hydrocarbon (PAH) and amino-PAH compounds to deoxyguanosine. Normal scanning provided structural information for a 1.3 ng injection of a model adduct, while 1.3 ng of each of a mixture of adducts was sufficient to determine their molecular weights by monitoring the constant neutral loss of deoxyribose. Exploitation of this loss in the multiple reaction monitoring mode resulted in the detection of low picogram amounts of target adducts in mixtures.

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Fast atom bombardment and collisional activation mass spectrometry as probes for the identification of positional isomers in a series of benzylated guanosines

Cited by 18 publications

References 44 publications

Identification of phenolics and nucleoside derivatives in Gastrodia elata by HPLC‐UV‐MS

Identification of phenolics and nucleoside derivatives in Gastrodia elata by HPLC‐UV‐MS

Application of capillary liquid chromatography coupled with tandem mass spectrometric methods to the rapid screening of adducts formed by the reaction of N-acetoxy-N-acetyl-2-aminofluorene with calf DNA

Identification of deoxynucleoside—polyaromatic hydrocarbon adducts by capillary zone electrophoresis—Continuous Flow-fast atom bombardment mass spectrometry

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