title: Complete (1)H and (13)C NMR chemical shift assignments of mono- to tetrasaccharides as basis for NMR chemical shift predictions of oligosaccharides using the computer program CASPER.
abstract: (1)H and (13)C NMR chemical shift data are used by the computer program CASPER to predict chemical shifts of oligo- and polysaccharides. Three types of data are used, namely, those from monosaccharides, disaccharides, and trisaccharides. To improve the accuracy of these predictions we have assigned the (1)H and (13)C NMR chemical shifts of eleven monosaccharides, eleven disaccharides, twenty trisaccharides, and one tetrasaccharide; in total 43 compounds. Five of the oligosaccharides gave two distinct sets of NMR resonances due to the α- and β-anomeric forms resulting in 48 (1)H and (13)C NMR chemical shift data sets. In addition, the pyranose ring forms of Neu5Ac were assigned at two temperatures, due to chemical shift displacements as a function of temperature. The (1)H NMR chemical shifts were refined using total line-shape analysis with the PERCH NMR software. (1)H and (13)C NMR chemical shift predictions were subsequently carried out by the CASPER program (http://www.casper.organ.su.se/casper/) for three branched oligosaccharides having different functional groups at their reducing ends, namely, a mannose-containing pentasaccharide, and two fucose-containing heptasaccharides having N-acetyllactosamine residues in the backbone of their structures. Good to excellent agreement was observed between predicted and experimental (1)H and (13)C NMR chemical shifts showing the utility of the method for structural determination or confirmation of synthesized oligosaccharides.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden.
authors.forename: Jerk
authors.initials: J
authors.lastname: Rönnols
authors.forename: Robert
authors.initials: R
authors.lastname: Pendrill
authors.forename: Carolina
authors.initials: C
authors.lastname: Fontana
authors.forename: Christoffer
authors.initials: C
authors.lastname: Hamark
authors.forename: Thibault Angles
authors.initials: TA
authors.lastname: d'Ortoli
authors.forename: Olof
authors.initials: O
authors.lastname: Engström
authors.forename: Jonas
authors.initials: J
authors.lastname: Ståhle
authors.forename: Mona V
authors.initials: MV
authors.lastname: Zaccheus
authors.forename: Elin
authors.initials: E
authors.lastname: Säwén
authors.forename: Liljan E
authors.initials: LE
authors.lastname: Hahn
authors.forename: Shahzad
authors.initials: S
authors.lastname: Iqbal
authors.forename: Göran
authors.initials: G
authors.lastname: Widmalm
mesh_terms: D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D009005:Monosaccharides / Q000737:chemistry*; D009844:Oligosaccharides / Q000737:chemistry*; D012984:Software
chemical_list: D009005:Monosaccharides; D009844:Oligosaccharides
keywords: Automation; Chemical shift prediction; Glycan; Oligosaccharide