Biotin[6]uril sulfone dimer: a water-soluble dimeric anion receptor
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| Year of publication | 2017 |
| Type | Appeared in Conference without Proceedings |
| MU Faculty or unit | |
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| 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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