Mechanistic considerations of the protonation and fragmentation of highly functionalized molecules in fast atom bombardment: High resolution mass spectrometry and tandem mass spectrometry analysis of the ions formed by fast atom bombardment of digoxin and related cardiac glycosides

Light, K.J.; Allison, John

doi:10.1016/1044-0305(90)85029-l

Cited by 10 publications

(1 citation statement)

References 25 publications

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“…1,2‐Eliminations of ROH (R = H, CH 3 or CH 3 CO) from protonated saccharides have been described before and lead to the introduction of the designation [M n ′ + H] + for the [M − n ROH + H] + ions 29, 30. We will follow from now on this designation, thus [(M + H)CH 3 COOH] + and [(M + H)2CH 3 COOH] + will be, respectively, [M′ + H] + and [M″ + H] + .…”

Section: Resultsmentioning

confidence: 99%

Gas‐phase fragmentation of protonated C₆₀‐pyrimidine derivatives

et al. 2009

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Electrospray ionization mass spectrometry/mass spectrometry (ESI/MS/MS) and multiple stage mass spectrometry (MSn, n > 2) were used in the positive ion mode, with two different types of mass spectrometers, a quadrupole time-of-flight and an ion trap, to characterize two sets of different types of C60-aminopyrimidine exohedral derivatives. In one set, the pyrimidine moiety bears an amino acid methyl ester residue, and in the other the pyrimidine ring is part of a nucleoside-type moiety, the latter existing as two separated diastereoisomers.We have found that retro-cycloaddition processes occur for the closed shell protonated species formed by electrospraying C60 derivatives synthesized by Diels-Alder reactions, whereas for the C60 derivatives synthesized via 1,3-dipolar cycloadditions, these processes did not occur. Formation of diagnostic ions allowed the differentiation between the two groups of fullerene derivatives, and between the diastereoisomers of C60 derivatives with a nucleoside-type moiety. In general, the fragmentation processes are strongly dependent on the protonation sites and on the structure of the exohedral moieties.

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Section: Resultsmentioning

confidence: 99%

Gas‐phase fragmentation of protonated C₆₀‐pyrimidine derivatives

et al. 2009

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Fragmentation behavior of disaccharides during desorption–ionization

Carroll

Lebrilla

1992

Org. Mass Spectrom.

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The fragmentation behavior of native and singly derivatized protonated disaccharides were examined by fast ion bombardment Fourier transform mass spectrometry to determine the origin of various fragment ions produced during desorption-ionization. The lack of interfering matrix ions in this technique allowed the investigation of model disaccharides. Three major product ions were observed, corresponding in mass to a loss of H,O, a loss of a monosaccharide unit and a combination of both losses. The oxygen of the lost H,O molecule originates from an oxygen attached to the anomeric carbon. The other two product ions come from two different monosaccharide units and are due to competing processes. The relative ion intensities of these two fragment ions are governed by the basicities of the fragments. The basicity of the reducing end increases when the hemiacetal is converted into the methyl glycoside. This increase in basicity is due to the increased size of the alkyl group and the ability of the alkyl group to prevent the opening of the reducing glycosidic ring.

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Collisional activation of metal cationized and deprotonated triterpenoids: Charge remote fragmentations

Madhusudanan

Singh

1992

Org. Mass Spectrom.

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The collisional activation spectra of lithiated and bariated cations and deprotonated anions of the triterpenoic acids hederagenin and oleanoic acid and their acetyl derivatives were examined. On collisional activation these precursors undergo similar charge-remote fragmentations including ring cleavage reactions and loss of substituents from the ring furthest from the site of charge. The presence of a double bond in ring C induces charge-remote retro-DielsAlder reaction in these molecules.

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Mechanistic considerations of the protonation and fragmentation of highly functionalized molecules in fast atom bombardment: High resolution mass spectrometry and tandem mass spectrometry analysis of the ions formed by fast atom bombardment of digoxin and related cardiac glycosides

Cited by 10 publications

References 25 publications

Gas‐phase fragmentation of protonated C₆₀‐pyrimidine derivatives

Gas‐phase fragmentation of protonated C₆₀‐pyrimidine derivatives

Fragmentation behavior of disaccharides during desorption–ionization

Collisional activation of metal cationized and deprotonated triterpenoids: Charge remote fragmentations

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Mechanistic considerations of the protonation and fragmentation of highly functionalized molecules in fast atom bombardment: High resolution mass spectrometry and tandem mass spectrometry analysis of the ions formed by fast atom bombardment of digoxin and related cardiac glycosides

Cited by 10 publications

References 25 publications

Gas‐phase fragmentation of protonated C60‐pyrimidine derivatives

Gas‐phase fragmentation of protonated C60‐pyrimidine derivatives

Fragmentation behavior of disaccharides during desorption–ionization

Collisional activation of metal cationized and deprotonated triterpenoids: Charge remote fragmentations

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Product

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Gas‐phase fragmentation of protonated C₆₀‐pyrimidine derivatives

Gas‐phase fragmentation of protonated C₆₀‐pyrimidine derivatives