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Fluorometric Recognition of Nucleotides within a Water‐Soluble Tetrahedral Capsule
Author(s) -
Plajer Alex J.,
Percástegui Edmundo G.,
Santella Marco,
Rizzuto Felix J.,
Gan Quan,
Laursen Bo W.,
Nitschke Jonathan R.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201814149
Subject(s) - supramolecular chemistry , chemistry , cationic polymerization , aqueous solution , covalent bond , molecular recognition , amine gas treating , combinatorial chemistry , nucleotide , fluorescence , molecule , organic chemistry , biochemistry , physics , quantum mechanics , gene
Abstract The design of aqueous probes and binders for complex, biologically relevant anions presents a key challenge in supramolecular chemistry. Herein, a tetrahedral assembly with cationic faces and corners is reported that is capable of discriminating between anionic and neutral guests in water. Electrostatic repulsion between subcomponents can be overcome by the addition of an anionic template, or generating a robust covalent framework by incorporating tris(2‐aminoethyl)amine (TREN). The resultant TREN‐capped, water‐soluble, fluorescent cage binds mono‐ and poly‐phosphoric esters, including nucleotides. Its covalent skeleton renders it stable at micromolar concentrations in water, enabling the fluorometric detection of biologically relevant guests in an aqueous environment. Selective supramolecular encapsulants, such as 1 , could enable new sensing applications, such as recognition of toxins and drugs, under biological conditions.