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Download fileFrom Mannose to Small Amphiphilic Polyol: Perfect Linearity Leads To Spontaneous Aggregation
journal contribution
posted on 10.02.2016, 16:44 authored by Tiina Saloranta, Anssi Peuronen, Johannes
M. Dieterich, Janne Ruokolainen, Manu Lahtinen, Reko LeinoTerminally
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.