Determination of methionine enantiomers by HPLC on the cyclofructan chiral stationary phase

Abstract

The enantiomeric separation of methionine by high performance liquid chromatography on various cyclofructan type chiral stationary phases in the polar-organic separation mode was studied. The effects of the mobile phase composition and temperature on the enantioselectivity of the enantiomers were investigated. The enantioselective separation was attained on the isopropylcarbamate cyclofructan 6 chiral stationary phase with methanol/acetonitrile/acetic acid/triethylamine (75/25/0.3/ 0.2 v/v/v/v) as a mobile phase. The low retention and no separation were observed on the dimethylphenyl carbamate cyclofructan 7 and naphthylethyl carbamate cyclofructan 6 chiral stationary phases. Three types of detection, low-wavelength UV, polarimetric, and circular dichroism, were used.The UV detection limit for enantiomers was 11 mg mL À1 (S/N ¼ 3) and the polarimetric and circular dichroism detection limits were 10 and 8 times lower. Good linearity was observed from 50 to 500 mg mL À1 . The proposed method was applied to determine D-and L-methionine in a dietary supplement sample.

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

“…An HPLC-based method was developed for the separation of methionine enantiomers applying CF-based CSPs in PO mode [ 47 ]. The optimized method using isopropyl carbamate CF-6 bonded onto 5 µm silica particles was validated and successfully applied for the quantitative determination of the enantiomers of methionine in a dietary supplement sample.…”

Recent development trends for chiral stationary phases based on chitosan derivatives, cyclofructan derivatives and chiral porous materials in high performance liquid chromatography

“…Figure 5 depicts the structures of CF6-P, CF6-RN and CF7-DMP. Afterwards, the same group also carried out numerous comparison studies on the chiral recognition ability of cyclofructan-based CSPs (IP-CF6, RN-CF6 and DMP-CF7, as well as cyclodextrin-based CSPs) for the separation of a wide range of racemic compounds, including some unique and novel compounds such as tetrahydrobenzimidazoles, biaryl atropisomers, ruthenium(II) polypyridyl complexes, 2-naphthol atropisomers, α-aryl ketones, and spirobrassinin [53,[58][59][60][61][62][63][64][65][66][67][68]. The research results showed that most of the chiral analytes studied were well separated on these F I G U R E 5 The structures of the cyclofructan-based CSPs used for IP-CF6, RN-CF6 and DMP-CF7 chiral selectors, which have good complementary enantioseparation for some analytes.…”

Highly sensitive determination of methionine by solvent‐based de‐emulsification dispersive liquid–liquid microextraction using bio‐stabilized silver nanoparticles

“…Amino acid analysis has a significant value in pharmaceutical, biochemical and clinical research [1]. Methionine (2‐amino‐4‐(methylthio) butanoic acid) (Figure S1) is an essential sulfur‐containing amino acid in the human body that has potential in protein synthesis and transmethylation reaction [2].…”