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@proceedings{1385206,
author = {Lízal, Tomáš and Andersen, Nicolaj N. and Eriksen, Kristina and Hansen, Nicolai S. B. and Lisbjerg, Mick and Šindelář, Vladimír and Pittelkow, Michael},
booktitle = {12th International Symposium on Macrocyclic and Supramolecular Chemistry, July 2-6, 2017, Cambridge, United Kingdom},
keywords = {Anion binding, Biotinuril,},
language = {eng},
title = {Biotin[6]uril sulfone dimer: a water-soluble dimeric anion receptor},
url = {http://www.rsc.org/events/detail/17933/international-symposium-on-macrocyclic-and-supramolecular-chemistry-ismsc-in-conjunction-with-isacs-challenges-in-organic-materials-and-supramolecular-chemistry},
year = {2017}
}
TY - CONF
ID - 1385206
AU - Lízal, Tomáš - Andersen, Nicolaj N. - Eriksen, Kristina - Hansen, Nicolai S. B. - Lisbjerg, Mick - Šindelář, Vladimír - Pittelkow, Michael
PY - 2017
TI - Biotin[6]uril sulfone dimer: a water-soluble dimeric anion receptor
KW - Anion binding, Biotinuril,
UR - http://www.rsc.org/events/detail/17933/international-symposium-on-macrocyclic-and-supramolecular-chemistry-ismsc-in-conjunction-with-isacs-challenges-in-organic-materials-and-supramolecular-chemistry
N2 - 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.
ER -
LÍZAL, Tomáš, Nicolaj N. ANDERSEN, Kristina ERIKSEN, Nicolai S. B. HANSEN, Mick LISBJERG, Vladimír ŠINDELÁŘ and Michael PITTELKOW. Biotin[6]uril sulfone dimer: a water-soluble dimeric anion receptor. In \textit{12th International Symposium on Macrocyclic and Supramolecular Chemistry, July 2-6, 2017, Cambridge, United Kingdom}. 2017.
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