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. 2024 Jan 12;26(1):106-109.
doi: 10.1021/acs.orglett.3c03715. Epub 2023 Dec 28.

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

Arico Del Mauro  1   2 , Jana Lapešová  1   2 , Carola Rando  1   2 , Vladimír Šindelář  1   2
Affiliations

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

Arico Del Mauro et al. Org Lett. .

Abstract

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Chemical structures of (a) biotin[6]uril, (b) dodecabenzylbambus[6]urils (BnBU), (c) an example of a previously reported monofunctionalized bambus[6]uril (Mono-BU), and (d) hybrid macrocycle 1.
Scheme 1
Scheme 1. Synthesis of Macrocycle 1
Figure 2
Figure 2
Crystal structure of the Cl–⊂1 complex. (a) Top view and (b) arrangement of the complex into supramolecular polymeric chains.
Figure 3
Figure 3
1H NMR (500 MHz, CD3CN, 298.15 K) spectra of (a) the [1]rotaxane 5 formed quantitatively in situ, (b) bis(acyloxy)iodate(I) 4, and (c) macrocycle 1. *Dioxane, #tetrabutylammonium, &acetonitrile.
See this image and copyright information in PMC

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