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

Tiina Saloranta, Anssi Peuronen, Johannes M. Dieterich, Janne Ruokolainen, Manu Lahtinen, Reko Leino*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

5 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)655-661
Number of pages7
JournalCrystal Growth and Design
Volume16
Issue number2
DOIs
Publication statusPublished - 3 Feb 2016
MoE publication typeA1 Journal article-refereed

Keywords

  • Nuclear magnetic resonance spectroscopy
  • X ray diffraction
  • Self assembly

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