Solution conformations of three small cluster oligosaccharide mimetics (SCOM) from D-glucosamine, D-altrosamine, and (-)-quinic acidARKIVOC
AbstractThree 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.
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Citation InformationQ. 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/