High-performance liquid chromatographic determination of α-aminonitrile enantiomers after derivatization with o-phthalaldehyde and chiral thiols

被引：1

作者：

Duchateau, ALL ^{[1
]}

Boesten, JMM ^{[1
]}

Christis, B ^{[1
]}

Eijnthoven, F ^{[1
]}

Henderickx, HJW ^{[1
]}

机构：

[1] DSM Resolve, NL-6160 MD Geleen, Netherlands

来源：

JOURNAL OF CHROMATOGRAPHY A | 2004年 / 1055卷 / 1-2期

关键词：

enantiomer separation; molecular modelling; derivatization; LC; alpha-aminonitrile;

D O I：

10.1016/j.chroma.2004.08.132

中图分类号：

Q5 [生物化学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

o-Phthalaldehyde in combination with chiral thiols is described as a chiral reagent for the resolution of the enantiomers of alpha-H-alpha-aminonitriles and alpha-alkyl-alpha-aminonitriles. Separation of the resulting diastereomers was carried out by reversed-phase chromatography and the derivatives were detected at UV 340 nm. The identity of the diastereomeric derivatives was confirmed by LC-MS. Among the chiral thiols tested, N-acetyl-D-penicillamine and beta-mercaptoisobutyric acid gave the best resolution for the alpha-aminonitriles studied. For quantitative enantiomeric excess determination, beta-mercaptoisobutyric acid was chosen as this thiol could be obtained in high enantiomeric purity from a commercial source. The rate of the reaction of various alpha-aminonitriles with o-phthalaldehyde and beta-mercaptoisobutyric acid was studied. The accuracy of the method was investigated by a comparison of theoretical and measured enantiomeric excess. (C) 2004 Elsevier B.V All fights reserved.

引用

页码：235 / 239

页数：5

共 34 条

[1]

DETERMINATION OF D-ASPARTATE AND L-ASPARTATE IN AMINO-ACID MIXTURES BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY AFTER DERIVATIZATION WITH A CHIRAL ADDUCT OF O-PHTHALDIALDEHYDE [J].