Open AccessFluorescent Molecular Cages with Sucrose and Cyclotriveratrylene Units for the Selective Recognition of Choline and Acetylcholine
Author(s) -
Łukasz Szyszka,
Marcin Górecki,
Piotr Cmoch,
Sławomir Jarosz
Publication year - 2021
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.1c00019
Subject(s) - chemistry , choline , acetylcholine , diastereomer , fluorescence , fluorescence spectroscopy , acetylcholine receptor , stereochemistry , selectivity , binding constant , titration , molecular recognition , receptor , binding site , biochemistry , organic chemistry , molecule , biology , physics , quantum mechanics , endocrinology , catalysis
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.