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KMID : 0370220210650030209
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Yakhak Hoeji
2021 Volume.65 No. 3 p.209 ~ p.216
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Enantiomer Separation of Chiral Amines and Amino Acid Esters on Polysaccharide Phenylcarbamates Derived Chiral Stationary Phases
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Adhikari Suraj
Bhandari Alisha
Lee Won-Jae
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Abstract
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We have developed an efficient chiral HPLC method for enantiomeric resolution of some chiral amines and α-amino acid esters as nitrobenzoxadiazole (NBD) derivatives on amylose and cellulose phenylcarbamates derived chiralstationary phases (CSPs) under simultaneous ultraviolet (UV) and fluorescence (FL) detection. The observedenantioselectivities were affected by the type of the analyte (amines or α-amino acid esters), backbone structure (celluloseor amylose) of the CSP used, and substituents of phenyl moiety on the chiral selector of CSP. Further, for same chiralselectors, coated type CSPs showed better enantiomeric separation than those observed for the covalently bonded typeCSPs. In general, for the enantiomeric resolution of chiral amines, Chiralpak IE and Chiralcel OD-H columns showed thehighest enantioselectivities. However, for resolution of α-amino acid esters, the performances of Chiralpak IA andChiralpak AD-H (or Lux Amylose-1) columns were superior to those of other CSPs used. In general, the degrees ofenantioselectivity for α-amino acid ethyl esters are greater than those for chiral amines. The developed analytical methodwas applied to determine the enantiomeric purity of two commercially available chiral amine and α-amino acid ester; theenantiomeric impurities were observed to be 0.35 and 0.05% for (S)-α-methylbenzylamine and (S)-leucine ethyl ester,respectively. The validation data obtained from intra- and inter-day accuracy assays for (S)-3,3-dimethyl-2-butylamine and(S)-leucine ethyl ester were 99.92-101.46 and 100.61-101.78%; and 100.05-102.12 and 101.25-102.73%, respectively; theintra- and interday precision assays in terms of relative standard deviation (% RSD) were found to be 0.96-1.57 and 0.81-1.91%; and 0.24-1.01% and 0.65-1.35%, respectively. Owing to the high accuracy and precision results, the developedanalytical method can prove to be useful for the enantiomeric separation of various chiral amines and amino acid estersas NBD derivatives using polysaccharide derived CSPs.
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KEYWORD
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Amino acid esters, Chiral amine, Chiral stationary phase, Enantiomer separation, Nitrobenzoxadiazole derivative
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