(13)C-NMR glycosylation effects in (1→3)-linked furanosyl-pyranosides

(13)C-NMR glycosylation effects in (1→3)-linked furanosyl-pyranosides

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 config...

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Veröffentlicht in:Carbohydrate research 2015-11, Vol.417, p.1-10
Hauptverfasser: Gerbst, Alexey G, Krylov, Vadim B, Vinnitskiy, Dmitry Z, Dmitrenok, Andrey S, Shashkov, Alexander S, Nifantiev, Nikolay E
Format: Artikel
Sprache:eng
Schlagworte:
Carbohydrate Conformation
Disaccharides - chemistry
Furans - chemistry
Glucosides - chemistry
Glycosylation
Magnetic Resonance Spectroscopy
Models, Molecular
Pyrans - chemistry
Quantum Theory
Thermodynamics
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Beschreibung
Zusammenfassung: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.
ISSN:1873-426X
DOI:10.1016/j.carres.2015.08.014