Enantioseparation of novel anti-inflammatory chiral sulfoxides with two cellulose dichlorophenylcarbamate-based chiral stationary phases and polar-organic mobile phase(s)

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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HPLC separation of panthenol enantiomers on different types of chiral stationary phases

Acta Chimica Slovaca ◽

10.2478/acs-2018-0017 ◽

2018 ◽

Vol 11 (2) ◽

pp. 114-119 ◽

Cited By ~ 1

Author(s):

Anna Lomenova ◽

Katarína Hroboňová ◽

Terézia Šolónyová

Keyword(s):

High Performance Liquid Chromatography ◽

Liquid Chromatography ◽

Mobile Phase ◽

High Performance ◽

Limit Of Detection ◽

Stationary Phases ◽

Pharmaceutical Preparations ◽

Chiral Stationary Phases ◽

Biologically Active ◽

Different Types

Abstract Panthenol is a biologically active compound closely related to vitamin B5 (pantothenic acid). This work deals with the separation of panthenol enantiomers using high performance liquid chromatography. Different types of chiral stationary phases (β-cyclodextrin, isopropyl carbamate cyclofructan 6, amylose tris(3,5-dimethylphenylcarbamate)) were tested in normal phase separation mode. Effect of mobile phase composition on the resolution and retention of enantiomers was studied. Two types of detectors, low-wavelength UV and polarimetric, were used. The optimal chromatographic system includes a chiral stationary phase based on amylose and a mobile phase of hexane/ethanol (60/40, v/v) where the resolution of enantiomers reached the value Rs = 2.49. Suitable chromatographic conditions were applied for the determination of panthenol enantiomers in samples of pharmaceutical preparations with the obtained recovery of more than 92 %. Linearity of the high performance liquid chromatography method with spectrophotometric detection was from 1.0 × 10−3 to 1.3 mg mL−1 (R2 = 0.998), with the limit of detection of 0.3 × 10−3 mg mL−1 for both enantiomers.

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