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Liquid chromatographic resolution of N‐acyl‐α‐amino acids as their anilide derivatives on a chiral stationary phase based on (S)‐leucine
Author(s) -
Hyun Myung Ho,
Lee Gil Soo,
Han Sang Cheol,
Cho Yoon Jae,
Baik In Kyu
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10109
Subject(s) - chemistry , enantiomer , amino acid , resolution (logic) , leucine , stereochemistry , chromatography , biochemistry , artificial intelligence , computer science
A chiral stationary phase (CSP 1 ) derived from N‐(3,5‐dinitrobenzoyl)leucine N‐phenyl N‐alkylamide was used for the liquid chromatographic resolution of anilide derivatives of N‐acyl‐α‐amino acids and the chromatographic resolution results were compared with those from four other commercial CSPs. The chromatographic resolution results showed that CSP 1 was most effective among five CSPs used in this study. The chiral recognition mechanism exerted by CSP 1 for the resolution of anilide derivatives of N‐acyl‐α‐amino acids is proposed to involve a face‐to‐face π–π interaction and two hydrogen bonding interactions between the CSP and the analytes from the chromatographic resolution behaviors of slightly modified anilide derivatives of N‐acyl‐α‐amino acids. The chiral recognition mechanism proposed is quite similar to that advanced previously for the resolution of N‐(3,5‐methoxybenzoyl)‐α‐amino acids on CSP 1 , even though the interaction sites of the two types of analytes were totally different from each other. The apparent similarity of the two chiral recognition mechanisms was assumed to stem from the identical interaction modes of the two types of analytes with the CSP. In addition, the dependence of the enantioselectivity of anilide derivatives of N‐acyl‐α‐amino acids on the length of the alkyl tail of the N‐acyl group of analytes was rationalized to stem from the intercalation of the N‐acyl group of the (R)‐enantiomer of analytes between the tethers of the CSP. Chirality 14:503–508, 2002. © 2002 Wiley‐Liss, Inc.