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



: Saloranta T, Peuronen A, Dieterich JM, Ruokolainen J, Lahtinen M, Leino R

Publisher: AMER CHEMICAL SOC

: 2016

: Crystal Growth and Design

: CRYSTAL GROWTH & DESIGN

: CRYST GROWTH DES

: 16

: 2

: 655

: 661

: 7

: 1528-7483

DOI: https://doi.org/10.1021/acs.cgd.5b01135


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.



Last updated on 2024-26-11 at 21:49