Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 7, Pages 5129-5141Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00019
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Funding
- Polish National Science Centre [UMO-2016/21/B/ST5/03382]
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The synthesis of four fluorescent diastereoisomeric molecular cages containing cyclotriveratrylene and sucrose moieties connected via naphthalene linkers is reported in this study. These diastereoisomers were found to be selective and efficient receptors for acetylcholine and choline. Among them, compound M-5a showed the highest selectivity value.
The synthesis of four fluorescent diastereoisomeric molecular cages containing cyclotriveratrylene and sucrose moieties connected via the naphthalene linkers is reported. These diastereoisomers were found to be selective and efficient receptors for acetylcholine and choline. Compound P-5a has a better affinity for choline over acetylcholine, while cage M-5a exhibits a higher association constant for acetylcholine over choline. The highest selectivity value was observed for compound M-5a (K-ACh/K-Ch = 3.1). Cages P-5a, P-5b, M-5a, and M-5b were fully characterized by the advanced NMR techniques, and ECD spectroscopy was supported by DFT calculations. The binding constants K-a of these receptors were determined by fluorescence titration experiments in acetonitrile.
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