Ursodeoxycholic Bile Acid as Building Unit of Unprecedented
Supramolecular Complexes

a 2017

Ursodeoxycholic Bile Acid as Building Unit of Unprecedented Supramolecular Complexes

JURČEK, Ondřej, Pia Yasmine JURČEK, Elina KALENIUS, Linnanto JUHA MATTI, Radek MAREK et. al.

Základní údaje

Originální název

Ursodeoxycholic Bile Acid as Building Unit of Unprecedented Supramolecular Complexes

Název česky

Ursodeoxycholová kyselina jako stavební jednotka bezpříkladných supramolekulárních komplexů

Autoři

JURČEK, Ondřej, Pia Yasmine JURČEK, Elina KALENIUS, Linnanto JUHA MATTI, Radek MAREK a Kari RISSANEN

Vydání

12th International Symposium on Macrocyclic and Supramolecular Chemistry (ISMSC 2017), 2017

Další údaje

Jazyk

angličtina

Typ výsledku

Konferenční abstrakt

Obor

10401 Organic chemistry

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Organizační jednotka

Středoevropský technologický institut

Klíčová slova anglicky

bile acid; supramolecular chemistry; coordination complex; chirality; transformation; palladium complex

Příznaky

Mezinárodní význam

Změněno: 16. 3. 2018 12:41, Ing. Ondřej Jurček, Ph.D. et Ph.D.

Anotace

V originále

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.

Návaznosti

5SA15055, interní kód MU

Název: Metal-Organic Materials for Pharmaceutical Applications (Akronym: MOPHARM)

Investor: Jihomoravský kraj, Metal-Organic Materials for Pharmaceutical Applications

Citovat

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

@proceedings{1411384,
   author = {Jurček, Ondřej and Jurček, Pia Yasmine and Kalenius, Elina and Juha Matti, Linnanto and Marek, Radek and Rissanen, Kari},
   booktitle = {12th International Symposium on Macrocyclic and Supramolecular Chemistry (ISMSC 2017)},
   keywords = {bile acid; supramolecular chemistry; coordination complex; chirality; transformation; palladium complex},
   language = {eng},
   title = {Ursodeoxycholic Bile Acid as Building Unit of Unprecedented Supramolecular Complexes},
   year = {2017}
}

TY  - CONF
ID  - 1411384
AU  - Jurček, Ondřej - Jurček, Pia Yasmine - Kalenius, Elina - Juha Matti, Linnanto - Marek, Radek - Rissanen, Kari
PY  - 2017
TI  - Ursodeoxycholic Bile Acid as Building Unit of Unprecedented Supramolecular Complexes
KW  - bile acid
KW  - supramolecular chemistry
KW  - coordination complex
KW  - chirality
KW  - transformation
KW  - palladium complex
N2  - 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.
ER  -

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

Podrobný výpis o publikaci