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 containing a single d-biotin and five glycoluril units. Host-guest properties of in chloroform solution and solid state were investigated. The macrocycle bearing a single functional group was employed in the formation of [1]rotaxane utilizing reversible covalent bonds.
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http://dx.doi.org/10.1021/acs.orglett.3c03715 | DOI Listing |
Nature
January 2025
Department of Chemistry, The University of Hong Kong, Hong Kong SAR, China.
Mimicking the superstructures and properties of spherical biological encapsulants such as viral capsids and ferritin offers viable pathways to understand their chiral assemblies and functional roles in living systems. However, stereospecific assembly of artificial polyhedra with mechanical properties and guest-binding attributes akin to biological encapsulants remains a formidable challenge. Here we report the stereospecific assembly of dynamic supramolecular snub cubes from 12 helical macrocycles, which are held together by 144 weak C-H hydrogen bonds.
View Article and Find Full Text PDFPlants (Basel)
December 2024
Departamento de Química, Universidad Técnica Particular de Loja (UTPL), Calle Paris s/n y Praga, Loja 110107, Ecuador.
This study presents the first chemical and enantioselective analyses of essential oils (EOs) derived from the leaves of two endemic species, Cuatrec. and (Kunth) Cass., from Loja, Ecuador.
View Article and Find Full Text PDFNanoscale
January 2025
CBMN, CNRS, UMR 5248, University of Bordeaux, 33600 Pessac, France.
Cast films of racemic helicene derivatives adsorbed onto the surface of nanometric silica helices with controlled handedness exhibited distinct CD signals, whereas no CD signal was observed in the absence of silica nanohelices. These CD signals originate from the helical supramolecular assemblies formed by the racemic mixture of helicenes, with no evidence of enantiospecific adsorption. Interestingly, when enantiomerically pure forms of these helicenes were drop-cast onto the silica helices, different CD spectra were observed depending on the combination of the helicenes' handedness with that of the silica nanohelices.
View Article and Find Full Text PDFChem Asian J
December 2024
Department of Chemistry, STSN Government Degree College, Kadiri, Sri Sathya Sai (Dist., Andhra Pradesh-515591, India.
The production of enantiomerically pure compounds remains a vital and valuable objective in modern organic chemistry due to their broad applications in fields such as biosensing, optics, electronics, photonics, catalysis, nanotechnology, and drug or DNA delivery. Optically pure α-hydroxy ketones, in particular, are key structural components in many drugs and natural products with significant biological activity. Among these, benzoin type α-hydroxy ketones, which possess two adjacent functional groups, a carbonyl and a hydroxy group, are especially important.
View Article and Find Full Text PDFCryst Growth Des
December 2024
Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, California 95064, United States.
Organometallic antimony(V) complexes were prepared as model compounds to better understand the interactions of chiral chelating diols with this metalloid. These complexes feature three aryl groups (-xylyl or -tolyl) and a bidentate -2,3-butanediolate. The -xylyl and -tolyl complexes of either enantiomerically pure 2,3-butanediolate or 2,3-butanediolate (compounds -) crystallized in Sohncke space groups, as expected.
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