1. A Many-Faced Alkaloid: Polymorphism of (-)-Monophyllidin.
- Author
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Dank C, Wurzer R, Felsinger S, Bugl R, Kählig H, Hela W, Roller A, and Gstach H
- Subjects
- Acetonitriles chemistry, Alkaloids chemical synthesis, Crystallography, X-Ray, Esters chemical synthesis, Esters chemistry, Ethanol chemistry, Hydrogen Bonding, Models, Molecular, Molecular Conformation, Oxygen chemistry, Solvents chemistry, Water chemistry, Alkaloids chemistry
- Abstract
The synthesis of the alkaloid (-)-monophyllidin is described. The molecule is a hybrid of xanthoxyline and (S)-proline, accessible in one-step through a Mannich reaction. In the solid-state, defined structural arrangements with different physical properties are formed. Single crystal X-ray diffraction revealed structures of six distinct polymorphs. In the crystalline state, the alkaloid can host small polar molecules (preferably water), while the (S)-proline moiety is present in the zwitterionic state. Combined with the chelate, which is already present in the xanthoxyline substructure, an ideal disposition for multiple hydrogen bond networks evolve. Therefore, highly water-soluble polymorphs of monophyllidin can form. This structural flexibility explains the many faces of the molecule in terms of structure as well as analytical data. Furthermore, speculations about the biological role of the molecule, with regard to the manifold interactions with water, are presented., Competing Interests: The authors declare no conflict of interest.
- Published
- 2020
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