From Mannose to Small Amphiphilic Polyol: Perfect Linearity Leads To Spontaneous Aggregation
Saloranta, T., Peuronen, A., Dieterich, J. M., Ruokolainen, J., Lahtinen, M., & Leino, R. (2016). From Mannose to Small Amphiphilic Polyol: Perfect Linearity Leads To Spontaneous Aggregation. Crystal Growth and Design, 16 (2), 655-661. doi:10.1021/acs.cgd.5b01135
Published inCrystal Growth and Design
DisciplineEpäorgaaninen ja analyyttinen kemia
© 2015 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by American Chemical Society. Published in this repository with the kind permission of the publisher.
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.