13C-NMR glycosylation effects in (1→3)-linked furanosyl-pyranosides. (19th November 2015)

• Record Type: Journal Article
• Authors: Gerbst, Alexey G.; Krylov, Vadim B.; Vinnitskiy, Dmitry Z.; Dmitrenok, Andrey S.; Shashkov, Alexander S.; Nifantiev, Nikolay E.
• Is Part Of: Carbohydrate research. Volume 417(2015)
• Page Start: 1
• Page End: 10
• Publication Date: 2015-11-19
• Subjects: 13C NMR chemical shifts -- 13C NMR glycosylation effects -- Furanosides -- Conformation analysis -- ab initio calculations; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2015.08.014
• Languages: English
• ISSNs: 0008-6215

Abstract

Highlights: Six (1→3)-linked furanosyl-pyranosides have been synthesized. 13 C NMR glycosylation effects have been measured for these compounds. Several conformers have been revealed during theoretical conformational analysis. These conformers are used to explain the observed glycosylation effects. Graphical abstract: 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.