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

Alexey G Gerbst; Vadim B Krylov; Dmitry Z Vinnitskiy; Andrey S Dmitrenok; Alexander S Shashkov; Nikolay E Nifantiev

doi:10.1016/j.carres.2015.08.014

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

Carbohydr Res. 2015 Nov 19:417:1-10. doi: 10.1016/j.carres.2015.08.014. Epub 2015 Aug 28.

Authors

Alexey G Gerbst¹, Vadim B Krylov¹, Dmitry Z Vinnitskiy¹, Andrey S Dmitrenok¹, Alexander S Shashkov¹, Nikolay E Nifantiev²

Affiliations

¹ Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia.
² 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.

PMID: 26382080
DOI: 10.1016/j.carres.2015.08.014

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.

Keywords: (13)C NMR chemical shifts; (13)C NMR glycosylation effects; Conformation analysis; Furanosides; ab initio calculations.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Disaccharides / chemistry*
Furans / chemistry*
Glucosides / chemistry*
Glycosylation
Magnetic Resonance Spectroscopy
Models, Molecular
Pyrans / chemistry*
Quantum Theory
Thermodynamics

Substances

Disaccharides
Furans
Glucosides
Pyrans