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Furanose C—C‐linked γ‐lactones: a combined ESI FTICR MS and semi‐empirical calculations study
Author(s) -
Amorim Madeira Paulo J.,
Xavier Nuno M.,
Rauter Amélia P.,
Florêncio M. Helena
Publication year - 2010
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.1806
Subject(s) - chemistry , fragmentation (computing) , furanose , protonation , electrospray ionization , moiety , lactone , stereochemistry , mass spectrometry , fourier transform ion cyclotron resonance , computational chemistry , ring (chemistry) , ion , organic chemistry , chromatography , computer science , operating system
Sugars that incorporate the unsaturated carbonyl motif have become important synthetic targets not only as a result of their potential biological properties but also as precursors in the synthesis of many bioactive products. Moreover, little is known about the influence of the γ‐lactone moiety in the fragmentation pattern of furanose rings. Therefore, two α,β‐unsaturated γ‐lactones (butenolides) and two β‐hydroxy γ‐lactones, CC linked to a furanose ring were studied using electrospray ionization FTICR mass spectrometry. The behaviour of the protonated and sodiated forms of the compounds under study has been compared considering their structural features. Fragmentation mechanisms were established and ion structures were proposed taking into account the MS 2 and MS 3 experiments, accurate mass measurements and semi‐empirical calculations. These inexpensive methods proved to be a valuable resource for proposing protonation sites and for the establishment of fragmentation pathways. Copyright © 2010 John Wiley & Sons, Ltd.