Elucidation of the enantioselective recognition mechanism of a penicillin G acylase-based chiral stationary phase towards a series of 2-aryloxy-2-arylacetic acids

Chirality ◽  
2006 ◽  
Vol 18 (8) ◽  
pp. 633-643 ◽  
Author(s):  
Gabriella Massolini ◽  
Giuseppe Fracchiolla ◽  
Enrica Calleri ◽  
Giuseppe Carbonara ◽  
Caterina Temporini ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Penicillin G Acylase ◽  
Penicillin G ◽  
Recognition Mechanism ◽  
Enantioselective Recognition ◽  
Arylacetic Acids

Evaluation of a penicillin G acylase-based chiral stationary phase towards a series of 2-aryloxyalkanoic acids, isosteric analogs and 2-arylpropionic acids

2002 ◽  
Vol 958 (1-2) ◽  
pp. 131-140 ◽  
Author(s):  
E. Calleri ◽  
G. Massolini ◽  
F. Loiodice ◽  
G. Fracchiolla ◽  
C. Temporini ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Penicillin G Acylase ◽  
Penicillin G

scholarly journals Achiral Molecular Recognition of Substituted Aniline Position Isomers by Crown Ether Type Chiral Stationary Phase

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 493
Author(s):  
Atsushi Ohnishi ◽  
Tohru Shibata ◽  
Tatsuya Imase ◽  
Satoshi Shinkura ◽  
Kanji Nagai
Keyword(s):  
Molecular Recognition ◽  
Crown Ether ◽  
Stationary Phase ◽  
Steric Hindrance ◽  
Quantum Chemical ◽  
Chiral Stationary Phase ◽  
Positional Isomers ◽  
Substituted Anilines ◽  
Recognition Mechanism ◽  
Aryl Amines

To understand the selectivity of the crown ether type chiral stationary phase (CSP), the retention selectivity for aniline and the positional isomers of substituted anilines were studied. In various substituted isomers, except nitroaniline, a remarkable decrease of retention due to steric hindrance was observed for the 2-substituted isomer. To determine the detailed molecular recognition mechanism, quantum chemical calculations were performed for the aggregates between the crown ether and the anilines. The results suggested that the 20-Crown-6, which includes a phenyl-substituted 1,1′-binaphthyl moiety, interacts with alkyl and aryl amines in an unconventional form different from the proposed one for 18-Crown-6.

scholarly journals Synthesis of a Novel Chiral Stationary Phase by (R)-1,1′-Binaphthol and the Study on Mechanism of Chiral Recognition

Symmetry ◽  
2018 ◽  
Vol 10 (12) ◽  
pp. 704 ◽  
Author(s):  
Yongxi Wang ◽  
Dandan Liu ◽  
Yili Zhang ◽  
Yanmei Tang ◽  
Jingfeng Zhao ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Recognition ◽  
Chiral Stationary Phase ◽  
Separation Mechanism ◽  
The Novel ◽  
Experimental Conditions ◽  
Element Analysis ◽  
Recognition Mechanism ◽  
New Material ◽  
Conjugated Compounds

(R)-6-Acrylic-BINOL CSP, a novel chiral stationary phase was prepared by (R)-Binaphthol (R-BINOL) by introducing the acrylic group into the 6-position of (R)-BINOL before bonding it to the surface of silica gel. The structure of the CSP was characterized by IR, SEM, and element analysis. This new material was tested for its potential as a CSP for HPLC under normal phase conditions, especially for conjugated compounds. Six solutes were chosen to evaluate the chiral separation ability of the novel CSP. The effects of the mobile phase and temperature on enantioseparation were studied, and the chiral recognition mechanism was also discussed. The results showed that the space adaptability and π-π stacking between the solutes and the CSP affected the retention and enantioseparation. The Van’t Hoff curve indicated that under the experimental conditions, the separation mechanism of six solutes did not change, which were all enthalpy driven.

Separation and detection of cyproconazole enantiomers and its stereospecific recognition with chiral stationary phase by high-performance liquid chromatography

The Analyst ◽  
2019 ◽  
Vol 144 (17) ◽  
pp. 5193-5200 ◽  
Author(s):  
Zongzhe He ◽  
Fengxu Wu ◽  
Weitong Xia ◽  
Lianshan Li ◽  
Kunming Hu ◽  
...  
Keyword(s):  
High Performance Liquid Chromatography ◽  
Liquid Chromatography ◽  
Stationary Phase ◽  
Analytical Method ◽  
High Performance ◽  
Chiral Stationary Phase ◽  
Recognition Mechanism

An optimal chiral analytical method of cyproconazole enantiomers was established based on BBD, and the stereospecific recognition mechanism was elucidated by docking.

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