Document Type
Article
Publication Title
ARKIVOC
Department
Chemistry
ISSN
1551-7012
Volume
2007
Issue
13
DOI
10.3998/ark.5550190.0008.d27
First Page
235
Last Page
251
Publication Date
1-1-2007
Abstract
Three small cluster oligosaccharide mimetics were synthesized, and their CDCl3 solution conformations were determined with NMR experiments. In this paper, we confirmed conformational similarities in rings A and B in all three compounds, and we provide the overall solution geometries. In all cases, an unusual cyclohexane twist-boat conformation with longrange 4 J-(W)-coupling was observed. The origin of the bias towards the twist-boat was attributed primarily to the fused ring system between the cyclohexane ring and the dioxacyclopentane (acetal) including hydrogen bonding. Temperature-annealed molecular dynamics simulations complemented the NMR experiments and supported the overall assignment.
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
Recommended Citation
Nguyen, Q. L.,
Olmstead, L.,
Bains, S.,
&
Franz, A. H.
(2007).
Solution conformations of three small cluster oligosaccharide mimetics (SCOM) from D-glucosamine, D-altrosamine, and (-)-quinic acid.
ARKIVOC, 2007(13), 235–251.
DOI: 10.3998/ark.5550190.0008.d27
https://scholarlycommons.pacific.edu/cop-facarticles/137
