Comparison of Bambusuril and Biotinuril recognition towards anions

Abstract
Biotin[6]uril has the capability of binding with monovalent anions such as Cl- and –SCN in
phosphate buffer at pH 7.5. The binding affinity of Biotin[6]uril for different anions (PhCO 2-,
CN-, PF6-, CH3CO2-, ClO4-) has been investigated in water by using phosphate buffer (100 mM) at
pH 7.5. Electrostatic potential of Biotin[6]uril receptor for various guests has monitored by
computational studies. Mass spectrometry was used to analyze the biotin[6]uril-anion complexes.
The cavity of biotin[6]uril receptor has greater capacity of binding for larger softer anions than
smaller harder anions. Because it depends upon the size and nature of anions. 1 Water proved to
be the best solvent for macrocycles to bind with anions. The binding affinity of bambusurils
shown in chloroform solvent up to 3×109 Lmol-1 for different anions. Anions also used as
template for the synthesis of bambusuril macrocycles. The ability of Bambusuril 5 to bind with
different anions into its hydrophobic cavity (F-, Cl-, CN-,IO4-,ReO4-,Br-,PF6-,I-,NO3-,ClO4-) via
electrostatic interaction has monitored. It showed higher affinity in the range of 1-10 3 Lmol-1 as
neutral receptor for various anions in pure water. The bambusuril-anion complex was analyzed
by using 1H NMR and MALDI-TOF techniques.2

1 Lisbjerg, M; Nielsen, B. E; Milhøj, B. O; Sauer, S. P. A; Pittelkow, M; Anion binding by

biotin [6] uril in water. Organic & Biomolecular Chemistry. 2015, 13(2), 369-373.
2 Yawer, M. A; Havel, V; Sindelar, V; A bambusuril macrocycle that binds anions in water
with high affinity and selectivity. Angewandte Chemie International Edition. 2015, 54(1), 276-
279.