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From Mannose to Small Amphiphilic Polyol: Perfect Linearity Leads To Spontaneous Aggregation

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journal contribution
posted on 10.02.2016, 16:44 authored by Tiina Saloranta, Anssi Peuronen, Johannes M. Dieterich, Janne Ruokolainen, Manu Lahtinen, Reko Leino
Terminally unsaturated and diastereochemically pure polyol derived from d-mannose shows spontaneous aggregation behavior in water solution. In order to study and clarify this unforeseen phenomenon, a conformational study based on NMR spectroscopy combined with ab initio structure analysis using the COSMO-solvation model was pursued. The results, together with X-ray diffraction studies, suggest a low energy linear conformation for this particular substrate both in solid states and in solution. For such small-sized acyclic carbohydrate derivatives, the linear conformation appears to be a key prerequisite for the unusual molecular self-assembly reported herein.