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Titolo:
Collisionally-induced dissociation mass spectra of organic sulfate anions
Autore:
Attygalle, AB; Garcia-Rubio, S; Ta, J; Meinwald, J;
Indirizzi:
Cornell Univ, Dept Chem & Chem Biol, Baker Lab, Ithaca, NY 14853 USA Cornell Univ Ithaca NY USA 14853 em Biol, Baker Lab, Ithaca, NY 14853 USA
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
fascicolo: 4, , anno: 2001,
pagine: 498 - 506
SICI:
1472-779X(200104):4<498:CDMSOO>2.0.ZU;2-8
Fonte:
ISI
Lingua:
ENG
Soggetto:
FAST-ATOM-BOMBARDMENT; LIQUID-CHROMATOGRAPHY; ELECTROSPRAY-IONIZATION; STEROID SULFATES; GAS-PHASE; SPECTROMETRY; SULFOTRANSFERASES; URINE; REARRANGEMENT; METABOLITES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
61
Recensione:
Indirizzi per estratti:
Indirizzo: Attygalle, AB Cornell Univ, Dept Chem & Chem Biol, Baker Lab, Ithaca, NY 14853 USA Cornell Univ Ithaca NY USA 14853 Lab, Ithaca, NY 14853 USA
Citazione:
A.B. Attygalle et al., "Collisionally-induced dissociation mass spectra of organic sulfate anions", J CHEM S P2, (4), 2001, pp. 498-506

Abstract

The collisionally-induced dissociation mass spectra of a variety of organic sulfate ester anions are described and mechanistically rationalized. A cyclic syn-elimination pathway, analogous to that of the Cope elimination, ispostulated for the commonly observed formation of bisulfate anion (HSO4-, m/z 97). Deuterium labeling experiments confirm that the proton transferredto oxygen during bisulfate elimination normally originates from the C-2 position, although examination of the spectra of polyfunctional steroids reveals that the proton abstracted may originate from more distant sites as well. Adamantyl, phenyl, and vinyl sulfate anions, which do not readily lend themselves to a cyclic syn-elimination, do not give rise to an mit 97 ion. Instead, these sulfates undergo both heterolytic and homolytic S-O bond cleavages to yield an m/z M - 80 anion, resulting from loss of neutral SO3, as well as an ion at mh 80, corresponding to SO3-., respectively. Sulfates that can give rise to a resonance stabilized radical by homolytic C-O bond fission, as exemplified by benzyl and linalyl sulfates, can be recognized by the formation of an m/z 96 (SO4-.) ion.

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Documento generato il 04/04/20 alle ore 12:19:30