Recent applications in chiral high performance liquid chromatography: A review

Cavazzini, Alberto; Pasti, Luisa; Massi, Alessandro; Marchetti, Nicola; Dondi, Francesco

doi:10.1016/j.aca.2011.08.038

Cited by 240 publications

(160 citation statements)

References 283 publications

Supporting

Mentioning

157

Contrasting

Unclassified

Order By: Relevance

“…Although there are many methods used to isolate enantiomers, liquid chromatography is a simple, sensitive and accurate method. Among the various HPLC methods, the application of chiral stationary phases (CSPs) has been known to be the most accurate, convenient, and economic method in terms of resolution 11 . In method development, the availability of durable, stable and high-performance CSP column is preferable in developing a rugged and reproducible method.…”

Section: -(Aminomethyl)-1-ethylpyrrolidinementioning

confidence: 99%

Development of an Efficient HPLC Method With Pre-Column Derivatization for Determination of Enantiomeric Purity of 2-(Aminomethyl)-1-Ethylpyrrolidine

Wang

Yao

Qian

et al. 2015

J. Chil. Chem. Soc.

View full text Add to dashboard Cite

The development of a simple and efficient analytical method for determination of enantiomeric purity of 2-(aminomethyl)-1-ethylpyrrolidine was presented. The method was based on pre-column derivatization of 2-(aminomethyl)-1-ethylpyrrolidine with 4-nitrobenzoic acid completing separation of the enantiomers on high performance liquid chromatographic (HPLC) chiral stationary phase (CSP). After optimizing all the effective parameters, the best performances were achieved on a Chiralcel OD-H analytical column (250 × 4.6 mm) using n-hexane: ethanol (98:2, v/v) containing 0.2% triethylamine as mobile phase with a flow rate of 1.0 mL min -1 at 25°C. Online UV and optical rotation (OR) detection was performed at 254 nm. The parameters which have an effect on chiral separation were investigated, including mobile phase additive, organic modifier type and concentration, column temperature and flow rate. The method was tested for precision, accuracy, linearity, limit of detection (LOD), limit of quantification (LOQ) and robustness. The present method is expected to be accurate, stable, rapid and sensitive and can be used for the determination of the enantiomeric purity of 2-(aminomethyl)-1-ethylpyrrolidine in bulk samples.

show abstract

Section: -(Aminomethyl)-1-ethylpyrrolidinementioning

confidence: 99%

Development of an Efficient HPLC Method With Pre-Column Derivatization for Determination of Enantiomeric Purity of 2-(Aminomethyl)-1-Ethylpyrrolidine

Wang

Yao

Qian

et al. 2015

J. Chil. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…Fendiline also contains a secondary amino group and, in this instance, it is expected to be resolved on CSP 1. In this study, we wish to report the resolution of fendiline and its analogues (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) shown in Figure 2 on CSP 1.…”

Section: Introductionmentioning

confidence: 99%

“…Among various methods, liquid chromatographic chiral stationary phase (CSP) method has been known to be one of the most accurate, convenient and economic means for the determination of enantiomeric composition of chiral drugs [4]. Various liquid chromatographic CSPs have been applied to the determination of enantiomeric composition of chiral compounds [5,6]. For example, CSPs based on polysaccharide derivatives [7], cyclodextrines [8], macrocyclic antibiotics [9,10], cyclofrutanes [11], chiral crown ethers [11][12][13][14] and other small molecules [15] were quite successful for the resolution of racemic compounds.…”

Section: Introductionmentioning

confidence: 99%

Liquid Chromatographic Resolution of Fendiline and Its Analogues on a Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid

Lee

Hyun

2014

Molecules

View full text Add to dashboard Cite

Abstract:Fendiline, an effective anti-anginal drug for the treatment of coronary heart diseases, and its sixteen analogues were resolved on a CSP based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. Fendiline was resolved quite well with the separation factor (α) of 1.25 and resolution (RS) of 1.55 when a mobile phase consisting of methanolacetonitrile-trifluoroacetic acid-triethylamine at a ratio of 80/20/0.1/0.5 (v/v/v/v) was used. The comparison of the chromatographic behaviors for the resolution of fendiline and its analogues indicated that the 3,3-diphenylpropyl group bonded to the secondary amino group of fendiline is important in the chiral recognition and the difference in the steric bulkiness between the phenyl group and the methyl group at the chiral center of fendiline is also important in the chiral recognition.

show abstract

“…Chiral separation in high-performance liquid chromatography (HPLC) is keeping to be of great interest in diverse areas such as the agrochemicals and pharmaceutical industry [1]. To achieve better resolution and improve chiral stationary phase, enantioseparation mechanisms have been studied extensively using various methods [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic and Extrathermodynamic Studies of Enantioseparation of Imidazolinone Herbicides on Chiralcel OJ Column

Lao

2013

ISRN Chromatography

View full text Add to dashboard Cite

A homologous series of chiral imidazolinone herbicide was previously resolved on Chiralcel OJ column in high performance liquid chromatography. However, the mechanism of the chiral separation remains unclear. In this study, chromatographic behaviors of five chiral imidazolinone herbicides were characterized by thermodynamic and extrathermodynamic methods in order to enhance the understanding of the chiral separation. Thermodynamic parameters of this study were derived from equilibrium constant ( ) that was estimated from the moment analysis of the chromatographic peak. Van't Hoff plots of (ln versus 1/ ) were linear at a range of 15-50 ∘ C, only nonlinear at a range of 5-15 ∘ C with n-hexane (0.1%, trifluoroacetic acid)-2-propanol 60/40 (v/v) mobile phase. The enantiomer retention on the chiral column was entropy-driven at a lower temperature (5 ∘ C) and enthalpy-driven at a higher temperature (10 to 50 ∘ C). Enantioseparations of four of the five imidazolinone herbicides were enthalpy-driven, only entropy-driven for imazaquin. Enantioseparation mechanisms were different in between 5-10 ∘ C and 15-50 ∘ C probably due to the conformational change of the OJ phase. Enthalpy-entropy compensation showed similar mechanisms in retention and chiral separation for the five (−) or (+) enantiomers. Several extrathermodynamic relationships were able to be extracted to address additivity of group contribution.

show abstract

Recent applications in chiral high performance liquid chromatography: A review

Cited by 240 publications

References 283 publications

Development of an Efficient HPLC Method With Pre-Column Derivatization for Determination of Enantiomeric Purity of 2-(Aminomethyl)-1-Ethylpyrrolidine

Development of an Efficient HPLC Method With Pre-Column Derivatization for Determination of Enantiomeric Purity of 2-(Aminomethyl)-1-Ethylpyrrolidine

Liquid Chromatographic Resolution of Fendiline and Its Analogues on a Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid

Thermodynamic and Extrathermodynamic Studies of Enantioseparation of Imidazolinone Herbicides on Chiralcel OJ Column

Contact Info

Product

Resources

About