Publication details

Biotin[6]uril sulfone dimer: a water-soluble dimeric anion receptor

Authors

LÍZAL Tomáš ANDERSEN Nicolaj N. ERIKSEN Kristina HANSEN Nicolai S. B. LISBJERG Mick ŠINDELÁŘ Vladimír PITTELKOW Michael

Year of publication 2017
Type Appeared in Conference without Proceedings
MU Faculty or unit

Faculty of Science

Citation
Description Biotin[6]uril is a water-soluble macrocyclic anion receptor containing six D-biotin units. It binds large soft anions such as I- in 1:1 binding mode. Oxidation of biotin[6]uril with H2O2 in acetic acid yields the biotinsulfone[6]uril macrocycle, which displays 2:1 binding mode, an anion is complexed between two biotinsulfone[6]uril macrocycles. Inspired by the pioneering work by Kubik on dimeric cyclopeptide receptors2, we decided to link two biotinsulfone[6]uril together to investigate how preorganization affects anion binding. The biotinsulfone[6]uril was monofunctionalized via an amide coupling to expose a thiol group, and the two macrocycles were connected by oxidation to a disulfide. The supramolecular properties of the dimer were studied by isothermal titration calorimetry and NMR spectroscopy showing that the dimer bind anions in a 1:1 stoichiometry.
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