Merging Bambus[6]uril and Biotin[6]uril into an Enantiomerically Pure Monofunctionalized Hybrid Macrocycle

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 sin...

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Bibliographic Details
Published in:Organic letters 2024-01, Vol.26 (1), p.106-109
Main Authors: Del Mauro, Arico, Lapešová, Jana, Rando, Carola, Šindelář, Vladimír
Format: Article
Language:English
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Letter
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03715