Revelation of the chiral recognition of alanine and leucine in an l-phenylalanine-based metal–organic framework

An l-phenylalanine-based Zn-MOF, namely [Zn2(l-Phe)2(bpe)2]n, was designed for experimentally revealing the chiral recognition mechanism to alanine and leucine by means of 13C CP MAS NMR spectroscopy, XPS and control experiment.

Enantioseparation, Stereochemical Assignment and Chiral Recognition Mechanism of Sulfoxide-Containing Drugs

The distinct pharmacodynamic and pharmacokinetic properties of enantiopure sulfoxide drugs have stimulated us to systematically investigate their chiral separation, stereochemical assignment, and chiral recognition mechanism. Herein, four clinically widely-used sulfoxide drugs were chosen and optically resolved on various chiral stationary phases (CSPs). Theoretical simulations including electronic circular dichroism (ECD) calculation and molecular docking were adopted to assign the stereochemistry and reveal the underlying chiral recognition mechanism. Our results showed that the sequence of calculated mean binding energies between each pair of enantiomers and CSP matched exactly with experimentally observed enantiomeric elution order (EEO). It was also found that the length of hydrogen bond might contribute dominantly the interaction between two enantiomers and CSP. We hope our study could provide a fresh perspective to explore the stereochemistry and chiral recognition mechanism of chiral drugs.

Controllable synthesis of cellulose benzoates for understanding of chiral recognition mechanism and fabrication of highly efficient chiral stationary phases

The core of enantioseparation is to combine the hydrophobic helical conformation of cellulose derivatives with weak non-enantioselective interactions.