Mass spectrometry of the trimethylsilyl derivatives of some cardiac aglycones and monoglycosides

Falkner, Fred C.; Frölich, Jürgen C.; Watson, J. Throck

doi:10.1002/oms.1210070204

Cited by 9 publications

(1 citation statement)

References 21 publications

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“…Aliphatically‐linked glucuronides, on the other hand, eliminate the intact sugar residue to leave a carbonium ion. Sterol glycosides, such as sitosterol (Knights, ) and cardiac glycosides (Falkner et al, ) fragment similarly with loss of the entire sugar.…”

Section: Trimethylsilyl Derivativesmentioning

confidence: 99%

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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This review describes the mass spectral fragmentation of trimethylsilyl (TMS) and related alkylsilyl derivatives used for preparing samples for analysis, mainly by combined gas chromatography and mass spectrometry (GC/MS). The review is divided into three sections. The first section is concerned with the TMS derivatives themselves and describes fragmentation of derivatized alcohols, thiols, amines, ketones, carboxylic acids and bifunctional compounds such as hydroxy‐ and amino‐acids, halo acids and hydroxy ethers. More complex compounds such as glycerides, sphingolipids, carbohydrates, organic phosphates, phosphonates, steroids, vitamin D, cannabinoids, and prostaglandins are discussed next. The second section describes intermolecular reactions of siliconium ions such as the TMS cation and the third section discusses other alkylsilyl derivatives. Among these latter compounds are di‐ and trialkyl‐silyl derivatives, various substituted‐alkyldimethylsilyl derivatives such as the tert‐butyldimethylsilyl ethers, cyclic silyl derivatives, alkoxysilyl derivatives, and 3‐pyridylmethyldimethylsilyl esters used for double bond location in fatty acid spectra. © 2019 Wiley Periodicals, Inc. Mass Spec Rev 0000:1–107, 2019

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Section: Trimethylsilyl Derivativesmentioning

confidence: 99%

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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Mass spectra of spirostanol and furostanol glycosides

Komori

Ida

Mutou

et al. 1975

Biol. Mass Spectrom.

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The electron impact mass spectra of twenty acetates and methylates of spirostanol and related furostanol glycosides of high molecular weight (above 650) have been investigated, and the most probable fragmentation patterns of the glycoside derivatives are presented. High resolution mass spectrometry provides useful information concerning the structures of both aglycone and sugar moieties as well as the molecular size of the oligoglycosides.

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Mass spectrometric analysis of cardiac glycosides by the desorption/ionization technique potassium ion ionization of desorbed species

Light¹,

Kassel²,

Allison³

1989

Biol. Mass Spectrom.

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The analysis of cardiac glycosides by the desorption/ionization (D/I) mass spectrometric technique potassium ion ionization of desorbed species (K+IDS) is presented. K+IDS mass spectra of digitonin, digoxin, digoxigenin, digitoxin and ouabain are discussed to demonstrate the capabilities of this D/I method. The K+IDS analysis consists of two steps: thermal desorption of neutral molecules representative of the analyte, followed by gas-phase addition of K+ ions to these species. Structural and molecular weight information of the cardiac glycosides is obtained with the K+IDS technique. The most intense peak in the K+IDS mass spectrum of an analyte, M, is frequently the [M]K+ ion. Interpretation of the K+IDS mass spectra is simple, since one thermal degradation mechanism dominates. This mechanism is a 1,2-elimination process. A variation of the original K+IDS technique, performed by changing the ionizing metal from K+ to Na+ (i.e. Na+IDS), is presented for the analysis of digoxin. The Na+IDS mass spectrum of digoxin contains more structural information than the K+IDS mass spectrum of that compound. This may lead to a means of controlling the types of information obtainable with this D/I technique by varying the cation that is thermionically generated. K+IDS analyses can be performed rapidly, no sample derivatization is necessary, no matrix is required and little instrument modification is necessary.

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Mass spectrometry of the trimethylsilyl derivatives of some cardiac aglycones and monoglycosides

Cited by 9 publications

References 21 publications

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Mass spectra of spirostanol and furostanol glycosides

Mass spectrometric analysis of cardiac glycosides by the desorption/ionization technique potassium ion ionization of desorbed species

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