1977Chemical and Pharmaceutical BulletinOpen access

New derivatization for liquid chromatographic resolution of amino acid enantiomers.

Junichi Goto, Masatoshi Hasegawa, Setsuko Nakamura, Kazutake Shimada, Toshio Nambara

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Abstract

A new method for liquid chromatographic resolution of amino acid enantiomers by the formation of diastereomers has been developed. A chiral reagent used for this purpose, (-)-α-methoxy-α-methyl-1-naphthaleneacetic acid (IIb), was readily prepared by fractionally crystallizing the (+)-α-methylbenzylamine salt. The diastereomers formed from amino acid methyl esters and IIb by the N, N'-dicyclohexylcarbodiimide method were efficiently resolved on the normal phase column.

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A new method for liquid chromatographic resolution of amino acid enantiomers by the formation of diastereomers has been developed. A chiral reagent used for this purpose, (-)-α-methoxy-α-methyl-1-naphthaleneacetic acid (IIb), was readily prepared by fractionally crystallizing the (+)-α-methylbenzylamine salt. The diastereomers formed from amino acid methyl esters and IIb by the N, N'-dicyclohexylcarbodiimide method were efficiently resolved on the normal phase column.

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Available abstract

A new method for liquid chromatographic resolution of amino acid enantiomers by the formation of diastereomers has been developed. A chiral reagent used for this purpose, (-)-α-methoxy-α-methyl-1-naphthaleneacetic acid (IIb), was readily prepared by fractionally crystallizing the (+)-α-methylbenzylamine salt. The diastereomers formed from amino acid methyl esters and IIb by the N, N'-dicyclohexylcarbodiimide method were efficiently resolved on the normal phase column.

Key concepts: Diastereomer, Chemistry, Enantiomer, Derivatization, Reagent, Chromatography, Resolution (logic), Chiral derivatizing agent

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