Separation of chiral primary amino compounds by forming a sandwiched complex in reversed-phase high performance liquid chromatography |
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Authors: | Chen Zhang Wei X HuangZhi Chen Abu M Rustum |
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Institution: | Global Quality Services-Analytical Science, Schering-Plough Corp., 1011 Morris Avenue, Union, NJ 07083, USA |
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Abstract: | Separation of chiral primary amino compounds was efficiently achieved under reversed-phase high performance liquid chromatography (RP-HPLC) conditions using a mixture of non-chiral crown ether (18-crown-6) and dimethyl-β-cyclodextrin (DM-β-CD) in the mobile phase. Under these conditions, the amino group of the chiral compound was protonated in a low pH mobile phase, and then interacted with 18-crown-6 and DM-β-CD to form a sandwiched complex 18-crown-6 + amine + CD]. Enantiomers of the compound in the sandwiched complex were separated with good enantioselectivity. Formation of the sandwiched complex among the chiral compound and additives in the mobile phase is a key step of the chiral separation. Four different chiral amino compounds namely, 1-aminoindan (AI), 1,2,3,4-tetrahydro-1-naphthylamine (THNA), tyrosine (Tyr), and phenylalanine (Phe), were selected to demonstrate the separation using the sandwiched complex mechanism in RP-HPLC. |
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Keywords: | Chiral separation Reversed-phase HPLC Primary amino compounds Sandwiched complex Non-chiral crown ether Dimethyl-β-cyclodextrin |
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