Enantioselective Recognition by a New Chiral Stationary Phase at the Receptor Level

1995 ◽  
Vol 60 (14) ◽  
pp. 4314-4315 ◽  
Author(s):  
Francesco Gasparrini ◽  
Domenico Misiti ◽  
Claudio Villani ◽  
Allen Borchardt ◽  
Matthew T. Burger ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Receptor Level ◽  
Enantioselective Recognition

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

scholarly journals Enantiomeric Separation and Molecular Modelling of Bioactive 4-aryl-3,4-dihydropyrimidin-2(1H)-one Ester Derivatives on Teicoplanin-Based Chiral Stationary Phase

Separations ◽  
2021 ◽  
Vol 9 (1) ◽  
pp. 7
Author(s):  
Isabella Bolognino ◽  
Antonio Carrieri ◽  
Rosa Purgatorio ◽  
Marco Catto ◽  
Rocco Caliandro ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Molecular Descriptors ◽  
Enantiomeric Separation ◽  
Normal Phase ◽  
Chiral Selector ◽  
X Ray ◽  
Enantioselective Recognition ◽  
Highly Active ◽  
Molecular Dynamics Calculations

The enantiomeric separation of 15 racemic 4-aryl-3,4-dihydropyrimidin-2(1H)-one (DHP) alkoxycarbonyl esters, some of which proved to be highly active as A2B adenosine receptor antagonists, was carried out by HPLC on ChirobioticTM TAG, a chiral stationary phase (CSP) bearing teicoplanin aglycone (TAG) as the chiral selector. The racemic compounds were separated under polar organic (PO) conditions. Preliminarily, the same selectands were investigated on three different Pirkle-type CSPs in normal-phase (NP) conditions. A baseline separation was successfully obtained on TAG-based CSPs for the majority of compounds, some of which achieved high enantioselectivity ratios (α > 2) in contrast with the smaller α values (1–1.5) and the lack of baseline resolution observed with the Pirkle-type CSPs. In particular, the racemic tetrazole-fused DHP ester derivatives, namely compounds 8 and 9, were separated on TAG-based HPLC columns with noteworthy α values (8.8 and 6.0, respectively), demonstrating the potential of the method for preparative purposes. A competition experiment, carried out with a racemic analyte (6) by adding N-acetyl-d-alanine (NADA) to the mobile phase, suggested that H-bonding interactions involved in the recognition of the natural dipeptide ligand d-Ala-d-Ala into the TAG cleft should be critical for enantioselective recognition of 4-aryl DHPs by TAG. The X-ray crystal structure of TAG was elucidated at a 0.77 Å resolution, whereas the calculation of molecular descriptors of size, polar, and H-bond interactions, were complemented with molecular docking and molecular dynamics calculations, shedding light on repulsive (steric effects) and attractive (H-bond—polar and apolar) interactions between 4-aryl DHP selectands and TAG chiral selectors.

Chiral drugs separation by a new antibiotics-based chiral stationary phase

2014 ◽  
Author(s):  
Chunye Liu ◽  
Yanqing Miao ◽  
Yihui Guo ◽  
Yinjuan An ◽  
Yunfang Li ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Chiral Drugs ◽  
New Antibiotics

Advances in polymer materials as chiral stationary phase

2016 ◽  
Vol 34 (1) ◽  
pp. 34 ◽  
Author(s):  
Rongji DAI ◽  
Huiting WANG ◽  
Weiwei SUN ◽  
Yulin DENG ◽  
Fang LV ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Polymer Materials

Immobilized cellulase (CBH I) as a chiral stationary phase for direct resolution of enantiomers

1990 ◽  
Vol 112 (11) ◽  
pp. 4573-4574 ◽  
Author(s):  
Per Erlandsson ◽  
Ingrid Marle ◽  
Lennart Hansson ◽  
Roland Isaksson ◽  
Goeran Pettersson ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Resolution Of Enantiomers ◽  
Immobilized Cellulase
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