Development of Fluorescent Chemosensors for Amino‐Sugars

Abstract

In this account, we describe the application of a series of multidentate BINOL‐based phosphoric acids for the fluorescence‐based chemosensing of amino sugars. To this end, we developed a novel synthetic protocol for three isomerically pure phosphoric acid monoesters of the type ArOP(O)(OH)2. These were investigated with respect to their binding towards amino sugars (glucosamine, galactosamine and mannosamine) in comparison to the previously reported diesters of the type (ArO)2P(O)(OH). We could find that the diesters show no significant binding, while the monoesters can be used as hosts for amino sugars. Indeed, one host selectively binds to galactosamine, while a second host binds both glucosamine and mannosamine. This allows the fluorescence‐based detection and discrimination of the amino sugars by a novel class of phosphate‐based supramolecular hosts.

Dual activity inhibition of threonine aspartase 1 by a single bisphosphate ligand

“…For applications in chemosensing and organocataylsis, we have recently established a library of structurally related, low molecular weight bis-and trisphosphates. [57][58][59][60] These organic, multivalent ligands are based on rigid aromatic backbones, which allows a control of the relative positioning of the anionic phosphate groups in space, possibly offering a way to inuence the strength and selectivity of binding to the NLS domain comprising clusters of lysine and arginine residues (Fig. 1B) by systematic structural variations.…”

“…60 In contrast to the diesters, the latter class of ligands could be successfully utilized as chemosensors for different amino sugars. [57][58][59] They partially even revealed selective binding to certain sugar species, but have not yet been tested for their interaction with cationic protein-residues. Notably, all of these hosts ligands are synthetically readily available also on gramscale which makes them exceptionally attractive for a broad range of potential biomedical applications.…”