Fluorescent Molecular Cages with Sucrose and Cyclotriveratrylene Units for the Selective Recognition of Choline and Acetylcholine | Zendy

Łukasz Szyszka | Zendy; Marcin Górecki | Zendy; Piotr Cmoch | Zendy; Sławomir Jarosz | Zendy

Open Access

Fluorescent 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 -

the 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) - choline , chemistry , acetylcholine , diastereomer , acetylcholine receptor , selectivity , fluorescence , fluorescence spectroscopy , stereochemistry , titration , binding constant , receptor , binding site , organic chemistry , biochemistry , 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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research