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Solution conformations of three small cluster oligosaccharide mimetics (SCOM) from D-glucosamine, D-altrosamine, and (-)-quinic acid
ARKIVOC
  • Q. L. Nguyen
  • L. Olmstead
  • S. Bains
  • Andreas H. Franz, University of the Pacific
Document Type
Article
Department
Chemistry
DOI
10.3998/ark.5550190.0008.d27
Publication Date
1-1-2007
Disciplines
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
Creative Commons Attribution 4.0
Citation Information
Q. L. Nguyen, L. Olmstead, S. Bains and Andreas H. Franz. "Solution conformations of three small cluster oligosaccharide mimetics (SCOM) from D-glucosamine, D-altrosamine, and (-)-quinic acid" ARKIVOC Vol. 2007 Iss. 13 (2007) p. 235 - 251 ISSN: 1551-7012
Available at: http://works.bepress.com/andreas-franz/53/