Enantioseparation and molecular modeling study of chiral amines as three naphthaldimine derivatives using amylose or cellulose trisphenylcarbamate chiral stationary phases |
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Authors: | Suraj Adhikari Swapnil Bhujbal Man-Jeong Paik Wonjae Lee |
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Institution: | 1. College of Pharmacy, Chosun University, Gwangju, South Korea;2. Department of Biomedical Sciences, College of Medicine, Chosun University, Gwangju, South Korea;3. College of Pharmacy, Sunchon National University, Suncheon, South Korea |
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Abstract: | This study describes the enantioseparation of three chiral amines as naphthaldimine derivatives, using normal phase HPLC with amylose and cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phases (CSPs). Three chiral amines were derivatized using three structurally similar naphthaldehyde derivatizing agents, and the enantioselectivity of the CSPs toward the derivatives was examined. The degree of enantioseparation and resolution was affected by the amylose or cellulose-derived CSPs and aromatic moieties as well as a kind of chiral amine. Especially, efficient enantiomer separation was observed for 2-hydroxynapthaldimine derivatives on cellulose-derived CSPs. Molecular docking studies of three naphthaldimine derivatives of leucinol on cellulose tris(3,5-dimethylphenylcarbamate) were performed to estimate the binding energies and conformations of the CSP–analyte complexes. The obtained binding energies were in good agreement with the experimentally determined enantioseparation and elution order. |
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Keywords: | chiral selector chiral stationary phase enantioseparation molecular docking naphthaldimine derivative polysaccharide phenylcarbamate |
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