Synthesis of Macrocyclic Receptors with Intrinsic Fluorescence Featuring Quinizarin Moieties

Abstract

Abstract:An unprecedented class of macrocycles with intrinsic fluorescence consisting of phenolic trimers and quinizarin is developed. Though they are lacking of strong hydrogen bonds as observed in calixarenes, the two examples introduced here adopt each a vase-like conformation with all four aromatic units pointing in one direction (syn orientation). This 'cone' conformation had been confirmed by NMR spectroscopy, molecular modelling and X-ray crystallography. The laminar, electron-rich fluorophore as part of the macrocycle allows additional contacts to enclosed guest molecules.3

Synthetic Receptors for the Recognition and Discrimination of Post‐Translationally Methylated Lysines

“…presented trisulfonatocalixarene 20 (Scheme ) as a tool for the photochemical sensing of trimethyllysines in biological media . Macrocycle 20 features intrinsic fluorescence, and the recognition and sensing processes tolerate various salts, metal ions and enzymatic cofactors.…”

“…It can be assumed that prospective receptors will be designed to be either specific or generic in their recognition behaviour; in both cases, with high Kme 0 /Kme x selectivity. As proposed by the author and co‐workers, macrocycles with intrinsic fluorescence could be one way forward . Furthermore, bioinformatics combined with molecular modelling and crystallographic approaches will help to design new generations of artificial antibodies for the recognition of the methyllysine motif.…”