Mass spectra of nucleoside derivatives

Dolhun, John J.; Wiebers, J. L.

doi:10.1002/oms.1210030515

Cited by 44 publications

(14 citation statements)

References 11 publications

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“…There have been other studies concerning the ionic Lewis acid chemistry of boranes in the gas phase [2l], but little systematic work on the Brensted chemistry. Borate and boronate derivatives have been used in mass spectrometry [22]. To further examine the ability of boron to stabilize adjacent anions, as well as to examine reactivity related to the Lewis acidity of such species in the gas phase, we have investigated the gas-phase ion chemistry of a number of borate and boronate esters by using pulsed ICR spectrometry.…”

Section: \1 \mentioning

confidence: 99%

Gas-phase ion-molecule chemistry of borate and boronate esters

Kiplinger

Crowder

Sorensen

et al. 1994

J. Am. Soc. Mass Spectrom.

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Borate esters B(OR)3 and boronate esters RB(OR)2 undergo ion-molecule reactions to yield both addition products (by an implied radiative emission mechanism), ligand exchange, and proton transfer products, in both positive and negative ion modes. Although an acidity for CH3B(OR)2 could not be determined, HOB(OR)2 has an acidity between acetaldehyde and nitromethane. In light of the negligible polar electron acceptor properties of the -B(OR)2 group, that functionality must therefore be one of the best resonance electron acceptor groups known, almost half again as effective as the nitro group.

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Section: \1 \mentioning

confidence: 99%

Gas-phase ion-molecule chemistry of borate and boronate esters

Kiplinger

Crowder

Sorensen

et al. 1994

J. Am. Soc. Mass Spectrom.

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“…Both these circumstances Ref. 15). We have previously shown16*' 1 that the alky- greatly hinder an interpretation of the results obtained.…”

Section: Resultsmentioning

confidence: 99%

Mass spectrometry of some modified nucleosides of the pyrimidine and purine series

Mikhailopulo¹,

Kalinichenko²,

Зайцева³

et al. 1982

Biol. Mass Spectrom.

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The mass spectral fragmentation patterns of some pyrimidine and adenine nucleosides modified in a carbohydrate moiety have been investigated. The position of the chlorine atom in a carbohydrate moiety is characterized in the mass spectrum by the following peaks. In the case of pyrimidine nucleosides the location of the chlorine atom at C‐3′ leads as a general fragmentation pathway to a loss of a Cl radical to yield ion a, which further decomposes into ions h, n and j having the composition base plus 30,68 and 56 mass units, respectively. The location of the chlorine atom at C‐2′ involves initial elimination of HCI to form the ion(s) p which are transformed into the characteristic O2,2′‐cyclo ion r. The latter is one of the most abundant ions in the mass spectra of O2,2′‐cyclonuleosides. In the case of adenine chlorodeoxynucleosides the principal fragmentation routes from the molecular ion involve (i) a loss of a Cl radical and, further, the elements of H2O and formaldehyde 5′‐CH2O result in the formation of the characteristic Ion n (b+68mass units); (ii) a reverse sequence of transformations of the molecular ion leading to ion n. An intense ion d containing a C‐1′–C‐2′ fragment of the carbohydrate ring with a substituent at C‐2′is of considerable interest in elucidating the isomeric structure of the adenine chlorodeoxynucleosides. The same ion d is informative in establishing the isomeric structure of adenine 2′,3′‐ and 3′,5′‐anhydronucleosides.

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“…Die Aufnahme von Massenspektren freier Nucleoside ist allerdings durch die geringe Fliichtigkeit dieser Verbindungsklasse sehr begrenzt 11). Methoden zur Bildung von Derivaten wie Trimethylsilylierung lo), Permethylierung 13) …”

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Massenspektrometrische Untersuchung von Analogen des Adenosins

König¹,

Zech²,

Uhmann³

et al. 1972

Chem. Ber.

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Mass Spectrometry of Adenosine AnaloguesThe mass spectra of 23 trifluoroacetylated analogues of adenosine differing in the sugar moiety are investigated. The u-and P-anomers show characteristic intensity differences in the molecular ion and in the fragment ions m/e 310 and 424 (in pentose derivatives) as well as in m / e 550 and 680 (in hexose derivatives). The intensity differences can be explained by steric effects. The orientation of the hydroxyl groups does not influence the fragmentation process to such a degree that it is possible to draw systematic conclusions. For the identification of conformational isomers it is necessary to measure reference spectra. The ring size of the sugar is indicated by unique but low intensity fragments at m/e 524 and 410 (in furanosides of pentose derivatives), m/e 524 and 295 (in furanosides of hexose derivatives) as well as a t m/e 508 and 433 (in pyranosides of hexose derivatives). Substitution a t C-I' in hexose derivatives is indicated by ions a t mle 496 and 386.Durch Anwendung der in der zweiten Halfte dieses Jahrhunderts entwickelten Methoden zur Strukturanalyse, wie Circulardichroismus 1,2), magnetischer Circular-

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Mass spectra of nucleoside derivatives

Cited by 44 publications

References 11 publications

Gas-phase ion-molecule chemistry of borate and boronate esters

Gas-phase ion-molecule chemistry of borate and boronate esters

Mass spectrometry of some modified nucleosides of the pyrimidine and purine series

Massenspektrometrische Untersuchung von Analogen des Adenosins

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