Chiral Recognition by Flexible Coordination Polymers of Ag⁺ with a Cysteine-Based Chiral Thiol Ligand That Bears a Binding Site

Abstract

We report a new scheme for chiral recognition using coordination polymers of Ag+ with a chiral thiol ligand that contains a binding group. N-Benzoyl-l-cysteine ethyl ester equipped with a boronic acid group at the para position of the phenyl ring forms coordination polymers with Ag+ in alkaline aqueous solutions that exhibit excellent selectivity toward a d-glucose enantiomer over l-glucose, while the coordination polymers from the d-cysteine-based thiol ligand are specific for l-glucose. It is assumed that a conformation change occurs upon interaction of a saccharide molecule with the polymeric chain receptor, for which the next binding is promoted, leading to the highly effective chiral recognition, despite the flexible nature of the polymeric receptor.

Recognition of d-Glucose in Water with Excellent Sensitivity, Selectivity, and Chiral Selectivity Using γ-Cyclodextrin and Fluorescent Boronic Acid Inclusion Complexes Having a Pseudo-diboronic Acid Moiety

“…However, this substantially complicates the syntheses. Although many chiroptical diboronic acid-based receptors exhibit changes in circular dichroism spectra, most of them show no fluorescence response. , James et al reported a fluorescent binaphthyl diboronic acid-based receptor for the chiral recognition of d -glucose in methanol/water (1/2) with a D/L fluorescence intensity ratio of only 1.93 . Heinrichs et al developed a chiral macrocyclic diboronic acid-based receptor that shows chiral selectivity for d -glucose with turn-off response in methanol/water (1/1), requiring seven steps of complicated synthesis .…”

Plasmon-Enhanced Antibacterial Activity of Chiral Gold Nanoparticles and In Vivo Therapeutic Effect

“…d -cysteine ( d -cys), an enantiomer of natural l -cysteine ( l -cys), has been proved to significantly inhibit the growth of Gram negative E. coli by inhibiting the activity of threonine deaminase, which may further affect the synthesis of isoleucine, leucine and valine in bacteria [ 36 , 37 , 38 ]. In spite of this, d -cys is not widely used in practical applications because of its inefficient antibacterial properties.…”

A new two-dimensional folding sheet-like coordination polymer assembled from cadmium(II) and (S)-2-(benzylamino)succinic acid: synthesis, structure and properties

“…Thus, the resulting aspartic acid derivatives combine a connecting module (carboxylate groups), a flexible module (succinic acid backbone), a rigid and functional module (conjugated aryl groups), as well as a chiral module (chiral C atom). They may be used as building blocks to assemble homochiral CPs, which are a promising class of materials with various applications in chirotechnology and optoelectronics (Dong et al, 2021;Wang et al, 2012;Wen et al, 2013;Kee & Ok, 2021).…”