title: Theoretical study of deprotonated glucopyranosyl disaccharide fragmentation.
abstract: Molecular orbital calculations were used to investigate the fragmentation of deprotonated glucopyranosyl disaccharides. Based on data from collisional activation and isotopic labeling experiments, fragmentation mechanisms are proposed, with calculated transition states being used to study the energetics of fragmentation. The calculations suggest that deprotonation at the C(2) hydroxyl of the non-reducing ring, following ring opening, may be important for disaccharide fragmentation. It is also shown that the stereochemistry at the 2-position of the non-reducing ring may have a significant effect on disaccharide fragmentation, particularly with regard to determination of the anomeric configuration.
authors.affiliation: Department of Chemistry, La Trobe University, Bundoora, Victoria 3083, Australia.
authors.forename: B
authors.initials: B
authors.lastname: Mulroney
authors.forename: J
authors.initials: J
authors.lastname: Barrie Peel
authors.forename: J C
authors.initials: JC
authors.lastname: Traeger
mesh_terms: D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000737:chemistry*; D005583:Fourier Analysis; D005947:Glucose; D005960:Glucosides / Q000737:chemistry*; D008958:Models, Molecular; D008962:Models, Theoretical; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D018629:Spectrometry, Mass, Secondary Ion / Q000379:methods
chemical_list: D004187:Disaccharides; D005960:Glucosides; D005947:Glucose