Linked Life Data

12892909

Source:http://linkedlifedata.com/resource/pubmed/id/12892909

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
8
pubmed:dateCreated
2003-8-1
pubmed:abstractText
Ion trap mass spectrometry has been used to structurally characterize and differentiate positional and stereo isomers of arylglycosides having potential antioxidant properties. The use of the self-ionization (SI) technique has allowed to evidence a strong reactivity of fragment ions produced from dissociations of the molecular ion towards the molecules introduced into the trap. Specific structural effects due to positional isomers and anomers have been also envisaged through the occurrence of bimolecular processes inside the ion trap analyzer. Under self-ionization conditions, even-electron ions are produced. The charge is retained on the sugar moiety, in agreement with its proton affinity higher than that of the substituted phenol moiety. Most of the fragmentation pathways involve elimination of acetic acid that protects the hydroxylic groups of the glycoside. SI also produces adduct ions, likely as covalent species, having higher m/z values than the molecular ion. The reaction site is mainly the double bond present in the pyranosidic ring. Even if some fragment ions have lost the initial stereochemistry, their formation can be related to the structure of the parent neutrals introduced into the cell. Collision-induced dissociation (CID) experiments, carried out on ions formed by ion-molecule reactions, have allowed to obtain further information on gas phase ion structures. The study of mass-selected ion-molecule reactions and their kinetics have evidenced a spectacularly different reactivity of the ion at m/z 111 towards the two anomers 2alpha and 2beta, with the latter showing a much more pronounced reactivity. The approach developed in this work revealed to be an useful tool in structural characterization, as well as in stereo and regiochemical differentiation of arylglycosides.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Aug
pubmed:issn
1044-0305
pubmed:author
pubmed:issnType
Print
pubmed:volume
14
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
851-61
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
2003
pubmed:articleTitle
Application of self-ionization for enhancing stereochemical and positional effects from arylglycosides under electron ionization conditions in an ion trap mass spectrometer.
pubmed:affiliation
Laboratoire de Chimie Structurale Organique et Biologique, UMR 7613 CNRS, Université Pierre et Marie Curie, Paris, France.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't