title: (13)C-NMR glycosylation effects in (1→3)-linked furanosyl-pyranosides.
abstract: Synthesis, theoretical conformational analysis (molecular mechanics and DFT calculations) and NMR spectral data including the (13)C-NMR glycosylation effects for six pairs of isomeric furanosyl-(1→3)-pyranosides with different anomeric and absolute configurations of furanosyl units as well as configurations of C2 and C4 in the pyranoside units are described. The determined (13)C-NMR glycosylation effects were shown to correlate with the pattern of intramolecular interactions around the inter-unit bonds.
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia.
authors.forename: Alexey G
authors.initials: AG
authors.lastname: Gerbst
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia.
authors.forename: Vadim B
authors.initials: VB
authors.lastname: Krylov
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia.
authors.forename: Dmitry Z
authors.initials: DZ
authors.lastname: Vinnitskiy
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia.
authors.forename: Andrey S
authors.initials: AS
authors.lastname: Dmitrenok
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Shashkov
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia. Electronic address: nen@ioc.ac.ru.
authors.forename: Nikolay E
authors.initials: NE
authors.lastname: Nifantiev
mesh_terms: D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D011714:Pyrans / Q000737:chemistry*; D011789:Quantum Theory; D013816:Thermodynamics
chemical_list: D004187:Disaccharides; D005663:Furans; D005960:Glucosides; D011714:Pyrans
keywords: (13)C NMR chemical shifts; (13)C NMR glycosylation effects; Conformation analysis; Furanosides; ab initio calculations