Quinine-Based Zwitterionic Chiral Stationary Phase as a Complementary Tool for Peptide Analysis: Mobile Phase Effects on Enantio- and Stereoselectivity of Underivatized Oligopeptides

Chirality ◽  
2015 ◽  
Vol 28 (1) ◽  
pp. 5-16 ◽  
Author(s):  
Federica Ianni ◽  
Roccaldo Sardella ◽  
Andrea Carotti ◽  
Benedetto Natalini ◽  
Wolfgang Lindner ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Mobile Phase ◽  
Chiral Stationary Phase ◽  
Peptide Analysis ◽  
Mobile Phase Effects

Cellulose Tris(3,5-Dimethylphenylcarbamate) Regioselectively Bonded to Small Pore Silica Gel as Chiral Stationary Phase for HPLC

2011 ◽  
Vol 117-119 ◽  
pp. 1361-1364
Author(s):  
Yi Jun Zhang ◽  
Cai Xia Dong ◽  
Jun Chen ◽  
Run Qiang Liu
Keyword(s):  
Stationary Phase ◽  
Silica Gel ◽  
Mobile Phase ◽  
High Performance ◽  
Chiral Stationary Phase ◽  
High Performance Liquid Chromatographic ◽  
Hydroxyl Group ◽  
Cellulose Derivatives ◽  
Terephthaloyl Chloride ◽  
Small Pore

A bifunctional reagent of terephthaloyl chloride was initially adopted as a spacer reagent to prepare the bonded types of chiral stationary phase (CSP) with cellulose derivatives. (3,5-dimethylphenyl)carbamates of cellulose (CDMPC) regioselectively bonded to small pore (3-aminopropyl)silica gel (APS) were prepared with terephthaloyl chloride as a spacer at the 6-position of the primary hydroxyl group on the glucose unit of cellulose. Enantioseparations of five racemic samples are evaluated on the prepared CSP under normal-phase high-performance liquid chromatographic mode with hexane- isopropylalcohol as the mobile phase. The influence of flow rates and mobile phase compositions on the resolution were investigated. The prepared stationary phase was exhibited an effective chiral recognition.

Enantioseparation of Cinacalcet, and its Two Related Compounds by HPLC with Self-Made Chiral Stationary Phases and Chiral Mobile Phase Additives

2019 ◽  
Vol 15 (2) ◽  
pp. 200-209
Author(s):  
Canyu Yang ◽  
Ji Li ◽  
Yanyun Yao ◽  
Chen Qing ◽  
Baochun Shen
Keyword(s):  
Stationary Phase ◽  
Mobile Phase ◽  
High Performance ◽  
Chiral Stationary Phase ◽  
Stationary Phases ◽  
Chiral Stationary Phases ◽  
Starting Material ◽  
Mobile Phase Additives ◽  
Chiral Mobile Phase Additives ◽  
Related Compounds

Background: Cinacalcet is one of the second-generation calcimimetics which consists of a chiral center. The pharmacological effect of R-cinacalcet is 1000 times greater than that of the Scinacalcet. As mentioned in many literatures, 1-(1-naphthyl)ethylamine is used as the starting material for the synthesis of cinacalcet. The absolute structure of cinacalcet is influenced by the starting materials. Methods: We present the chiral separation of cinacalcet and its starting material, 1-(1-naphthyl) ethylamine along with one of its intermediates, N-(1-(naphthalen-1-yl) ethyl)-3- (3-(trifluoromethyl) phenyl) propanamide by high-performance liquid chromatography with chiral stationary phase and chiral mobile phase additives. Results: On vancomycin and cellulose tri 3,5-dimethylphenylcarbamate) chiral stationary phase, cinacalcet and 1-(1-naphthyl)ethylamine achieved enantioseparation under normal phase with addition of triethylamine additives, respectively. Meanwhile, 1-(1-naphthyl)ethylamine and N-(1-(naphthalen-1- yl)ethyl)-3-(3-(trifluoromethyl) phenyl) propanamide achieved enantioseparation on 1-napthalene vancomycin chiral stationary phase using D-tartaric acid, diethyl L-tartrate and diethyl D-tartrate as chiral mobile phase additives. Conclusion: The chiral recognition in our experiment was based on the hydrogen-bonding, dipoledipole and π-π interactions among the solutes, chiral stationary phases and chiral mobile phase additives. In addition, the space adaptability of chiral stationary phases also affected the separation efficacy.

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