Conformational Preferences of Ethyl 2,3-Dideoxy-3-[(α-D-glucopyranosyl)methyl]-β-L- and -D-arabino-hexopyranosides

[img]PDF - Authorized users only
Language: English
775Kb
Title:Conformational Preferences of Ethyl 2,3-Dideoxy-3-[(α-D-glucopyranosyl)methyl]-β-L- and -D-arabino-hexopyranosides
Creators:
Vích, Ondřej
Kniežo, Ladislav
Dvořáková, Hana
Raich, Ivan
Valenta, Štěpán
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 12, pp. 2086-2100
Uncontrolled Keywords:<i>C</i>-Disaccharides, <i>C</i>-Glycosides, MM3 calculations, Conformational analysis, NMR spectroscopy, Carbohydrates

Abstract

Conformational behavior of two <i>C</i>-disaccharides, containing D-glucopyranose moiety at the non-reducing end and L- or D-2-deoxy-<i>arabino</i>-hexopyranose moiety at the reducing end, has been studied using MM3 calculations and NMR experiments. The obtained results show that the conformational preference around the <i>C</i>-glycosidic bond is the same in both compounds and corresponds with the <i>exo</i>-anomeric effect. On the other hand, both compounds differ markedly in the conformational arrangement around the <i>C</i>-aglycone bond where the population of conformers is controlled by 1,3-diaxial-like interactions. <p>

Title:Conformational Preferences of Ethyl 2,3-Dideoxy-3-[(α-D-glucopyranosyl)methyl]-β-L- and -D-arabino-hexopyranosides
Creators:
Vích, Ondřej
Kniežo, Ladislav
Dvořáková, Hana
Raich, Ivan
Valenta, Štěpán
Uncontrolled Keywords:<i>C</i>-Disaccharides, <i>C</i>-Glycosides, MM3 calculations, Conformational analysis, NMR spectroscopy, Carbohydrates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:70
Number:12
Page Range:pp. 2086-2100
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20052086UNSPECIFIED
ID Code:2458
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Vích, Ondřej; Kniežo, Ladislav; Dvořáková, Hana; Raich, Ivan; Valenta, Štěpán (2005) Conformational Preferences of Ethyl 2,3-Dideoxy-3-[(α-D-glucopyranosyl)methyl]-β-L- and -D-arabino-hexopyranosides. Collection of Czechoslovak Chemical Communications, 70 (12). pp. 2086-2100. ISSN 0010-0765

Repository Staff Only: item control page