Bambus[6]urils and biotin[6]urils are macrocycles with an exceptional affinity for inorganic anions. Here, we investigated statistical condensation of 2,4-dibenzylglycoluril and d-biotin, monomers of the corresponding macrocycles, to prepare the enantiomerically pure macrocycle 1 containing a single d-biotin and five glycoluril units. Host-guest properties of 1 in chloroform solution and solid state were investigated. The macrocycle 1 bearing a single functional group was employed in the formation of [1]rotaxane utilizing reversible covalent bonds.

Department of Chemistry Faculty of Science Masaryk University 625 00 Brno Czech Republic

RECETOX Faculty of Science Masaryk University 625 00 Brno Czech Republic

Zobrazit více v PubMed

Šindelář V.; Lízal T.. Chapter 20. Hemicucurbiturils. In Monographs in Supramolecular Chemistry; Kim K., Ed.; Royal Society of Chemistry: Cambridge, U.K., 2019; pp 527–545.10.1039/9781788015967-00527 DOI

Lizal T.; Sindelar V. Bambusuril Anion Receptors. Isr. J. Chem. 2018, 58 (3–4), 326–333. 10.1002/ijch.201700111. DOI

Lisbjerg M.; Pittelkow M.. Hemicucurbit[n]Urils. Comprehensive Supramolecular Chemistry II; Elsevier: 2017; pp 221–236.10.1016/B978-0-12-409547-2.12515-6 DOI

Aav R.; Shmatova E.; Reile I.; Borissova M.; Topić F.; Rissanen K. New Chiral Cyclohexylhemicucurbit[6]Uril. Org. Lett. 2013, 15 (14), 3786–3789. 10.1021/ol401766a. PubMed DOI

Miyahara Y.; Goto K.; Oka M.; Inazu T. Remarkably Facile Ring-Size Control in Macrocyclization: Synthesis of Hemicucurbit[6]Uril and Hemicucurbit[12]Uril. Angew. Chem., Int. Ed. 2004, 43 (38), 5019–5022. 10.1002/anie.200460764. PubMed DOI

Kaabel S.; Adamson J.; Topić F.; Kiesilä A.; Kalenius E.; Öeren M.; Reimund M.; Prigorchenko E.; Lõokene A.; Reich H. J.; Rissanen K.; Aav R. Chiral Hemicucurbit[8]Uril as an Anion Receptor: Selectivity to Size, Shape and Charge Distribution. Chem. Sci. 2017, 8 (3), 2184–2190. 10.1039/C6SC05058A. PubMed DOI PMC

Lisbjerg M.; Jessen B. M.; Rasmussen B.; Nielsen B. E.; Madsen A. Ø.; Pittelkow M. Discovery of a Cyclic 6 + 6 Hexamer of D-Biotin and Formaldehyde. Chem. Sci. 2014, 5 (7), 2647.10.1039/C4SC00990H. DOI

Lisbjerg M.; Nielsen B. E.; Milhøj B. O.; Sauer S. P. A.; Pittelkow M. Anion Binding by Biotin[6]Uril in Water. Org. Biomol. Chem. 2015, 13 (2), 369–373. 10.1039/C4OB02211D. PubMed DOI

Yawer M. A.; Havel V.; Sindelar V. A Bambusuril Macrocycle That Binds Anions in Water with High Affinity and Selectivity. Angew. Chem., Int. Ed. 2015, 54, 276–279. 10.1002/anie.201409895. PubMed DOI

Fiala T.; Sleziakova K.; Marsalek K.; Salvadori K.; Sindelar V. Thermodynamics of Halide Binding to a Neutral Bambusuril in Water and Organic Solvents. J. Org. Chem. 2018, 83 (4), 1903–1912. 10.1021/acs.joc.7b02846. PubMed DOI

Itterheimová P.; Bobacka J.; Šindelář V.; Lubal P. Perchlorate Solid-Contact Ion-Selective Electrode Based on Dodecabenzylbambus[6]Uril. Chemosensors 2022, 10 (3), 115.10.3390/chemosensors10030115. DOI

Kuhl G. M.; Banning D. H.; Fargher H. A.; Davis W. A.; Howell M. M.; Zakharov L. N.; Pluth M. D.; Johnson D. W. Benchmarking the Placement of Hydrosulfide in the Hofmeister Series Using a Bambus[6]Uril-Based ChemFET Sensor. Chem. Sci. 2023, 14, 10273.10.1039/D3SC03616B. PubMed DOI PMC

Lang C.; Mohite A.; Deng X.; Yang F.; Dong Z.; Xu J.; Liu J.; Keinan E.; Reany O. Semithiobambus[6]Uril Is a Transmembrane Anion Transporter. Chem. Commun. 2017, 53 (54), 7557–7560. 10.1039/C7CC04026A. PubMed DOI

Khurana R.; Yang F.; Khurana R.; Liu J.; Keinan E.; Reany O. Semiaza -Bambusurils Are Anion-Specific Transmembrane Transporters. Chem. Commun. 2022, 58 (19), 3150–3153. 10.1039/D2CC00144F. PubMed DOI

Valkenier H.; Akrawi O.; Jurček P.; Sleziaková K.; Lízal T.; Bartik K.; Šindelář V. Fluorinated Bambusurils as Highly Effective and Selective Transmembrane Cl-/HCO3- Antiporters. Chem 2019, 5 (2), 429–444. 10.1016/j.chempr.2018.11.008. DOI

Rando C.; Vázquez J.; Sokolov J.; Kokan Z.; Nečas M.; Šindelář V. Highly Efficient and Selective Recognition of Dicyanoaurate(I) by a Bambusuril Macrocycle in Water. Angew. Chem., Int. Ed. 2022, 61 (43), e20221018410.1002/anie.202210184. PubMed DOI

Kokan Z.; Dušková-Smrčková M.; Šindelář V. Supramolecular Hydrogelation via Host-Guest Anion Recognition: Lamellar Hydrogel Materials for the Release of Cationic Cargo. Chem 2021, 7 (9), 2473–2490. 10.1016/j.chempr.2021.06.024. DOI

Reany O.; Mohite A.; Keinan E. Hetero-Bambusurils. Isr. J. Chem. 2018, 58 (3–4), 449–460. 10.1002/ijch.201700138. DOI

Singh M.; Solel E.; Keinan E.; Reany O. Dual-Functional Semithiobambusurils. Chem. Eur. J. 2015, 21 (2), 536–540. 10.1002/chem.201404210. PubMed DOI

Singh M.; Solel E.; Keinan E.; Reany O. Aza-Bambusurils En Route to Anion Transporters. Chem. Eur. J. 2016, 22 (26), 8848–8854. 10.1002/chem.201600343. PubMed DOI

Solel E.; Singh M.; Reany O.; Keinan E. Enhanced Anion Binding by Heteroatom Replacement in Bambusurils. Phys. Chem. Chem. Phys. 2016, 18 (19), 13180–13185. 10.1039/C6CP00442C. PubMed DOI

Maršálek K.; Šindelář V. Monofunctionalized Bambus[6]Urils and Their Conjugates with Crown Ethers for Liquid-Liquid Extraction of Inorganic Salts. Org. Lett. 2020, 22 (4), 1633–1637. 10.1021/acs.orglett.0c00216. PubMed DOI

De Simone N. A.; Chvojka M.; Lapešová J.; Martínez-Crespo L.; Slávik P.; Sokolov J.; Butler S. J.; Valkenier H.; Šindelář V. Monofunctionalized Fluorinated Bambusurils and Their Conjugates for Anion Transport and Extraction. J. Org. Chem. 2022, 87 (15), 9829–9838. 10.1021/acs.joc.2c00870. PubMed DOI

Del Mauro A.; Kokan Z.; Šindelář V. Dynamic [1]Rotaxanes via a Reversible Covalent Bond and Host-Guest Anion Recognition. Chem. Commun. 2022, 58 (23), 3815–3818. 10.1039/D2CC00779G. PubMed DOI

Havel V.; Sindelar V. Anion Binding Inside a Bambus[6]Uril Macrocycle in Chloroform. ChemPlusChem. 2015, 80 (11), 1601–1606. 10.1002/cplu.201500345. PubMed DOI