Ursodeoxycholic Bile Acid as Building Unit of Unprecedented Supramolecular Complexes

JURČEK, Ondřej, Pia Yasmine JURČEK, Elina KALENIUS, Linnanto JUHA MATTI, Radek MAREK and Kari RISSANEN. Ursodeoxycholic Bile Acid as Building Unit of Unprecedented Supramolecular Complexes. In 12th International Symposium on Macrocyclic and Supramolecular Chemistry (ISMSC 2017). 2017.

Basic information

• Original name: Ursodeoxycholic Bile Acid as Building Unit of Unprecedented Supramolecular Complexes
• Name in Czech: Ursodeoxycholová kyselina jako stavební jednotka bezpříkladných supramolekulárních komplexů
• Authors: JURČEK, Ondřej, Pia Yasmine JURČEK, Elina KALENIUS, Linnanto JUHA MATTI, Radek MAREK and Kari RISSANEN.
• Edition: 12th International Symposium on Macrocyclic and Supramolecular Chemistry (ISMSC 2017), 2017.

Other information

• Original language: English
• Type of outcome: Conference abstract
• Field of Study: 10401 Organic chemistry
• Country of publisher: United Kingdom of Great Britain and Northern Ireland
• Confidentiality degree: is not subject to a state or trade secret
• Organization unit: Central European Institute of Technology
• Keywords in English: bile acid; supramolecular chemistry; coordination complex; chirality; transformation; palladium complex
• Tags: International impact

Abstract

Large, non-symmetrical, inherently chiral bispyridyl ligand (L) derived from natural ursodeoxycholic bile acid was used in coordination to square-planar tetravalent Pd(II) yielding the cationic enantiomer of Pd3L6 coordination complex (1) containing 60 well-defined chiral centers in its flower-like structure. Complex 1 can be readily transformed by addition of chloride into a smaller enantiomerically pure metallacycle Pd3L3Cl6 (2). This transformation is reversible and can be restored by the addition of silver cations. Furthermore, a mixture of two constitutional isomers of the trimer, 2 and 2’, can be obtained by direct coordination of L to trans-N-pyridyl-coordinating Pd(II). These intriguing supramolecular assemblies have been thoroughly described by combination of various methods. The interconversion between particular species was followed by 1H NMR and mass spectrometry. The dimensions of complexes determined by 1H DOSY NMR spectroscopy and drift tube ion-mobility mass spectrometry agree well with molecular models. Variable temperature 1H NMR experiment was carried out to study the thermodynamic equilibria between 2 and 2’ complexes. The thermodynamic data obtained from the van’t Hoff plot agree well with computational calculations.

Links

• 5SA15055, interní kód MU: Name: Metal-Organic Materials for Pharmaceutical Applications (Acronym: MOPHARM)

Investor: South-Moravian Region