title: Complete assignments of the (1)H and (13)C chemical shifts and J(H,H) coupling constants in NMR spectra of D-glucopyranose and all D-glucopyranosyl-D-glucopyranosides.
abstract: Complete assignment of the (1)H and (13)C NMR spectra of all possible d-glucopyranosyl-d-glucopyranosides was performed and the (1)H chemical shifts and proton-proton coupling constants were refined by computational spectral analyses (using PERCH NMR software) until full agreement between the calculated and experimental spectra was achieved. To support the experimental results, the (1)H and (13)C chemical shifts and the spin-spin coupling constants between the non-hydroxyl protons of alpha- and beta-d-glucopyranose (1a and 1b) were calculated with density functional theory (DFT) methods at the B3LYP/pcJ-2//B3LYP/6-31G(d,p) level of theory. The effects of different glycosidic linkage types and positions on the glucose ring conformations and on the alpha/beta-ratio of the reducing end hydroxyl groups were investigated. Conformational analyses were also performed for anomerically pure forms of methyl d-glucopyranosides (13a and 13b) and fully protected derivatives such as 1,2,3,4,6-penta-O-acetyl-d-glucopyranoses (14a and 14b).
authors.affiliation: Laboratory of Organic Chemistry, Abo Akademi University, FI-20500 Abo, Finland. mattias_roslund@yahoo.com
authors.forename: Mattias U
authors.initials: MU
authors.lastname: Roslund
authors.forename: Petri
authors.initials: P
authors.lastname: Tähtinen
authors.forename: Matthias
authors.initials: M
authors.lastname: Niemitz
authors.forename: Rainer
authors.initials: R
authors.lastname: Sjöholm
mesh_terms: D002236:Carbohydrate Conformation; D002247:Carbon Isotopes; D006027:Glycosides / Q000737:chemistry*; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods*
chemical_list: D002247:Carbon Isotopes; D006027:Glycosides