色谱

色谱 ›› 2011, Vol. 29 ›› Issue (04): 368-372.DOI: 10.3724/SP.J.1123.2011.00368

• 技术与应用 • 上一篇    

9-蒽醛衍生化-高效液相色谱法拆分α-氨基酸甲酯和几种脂肪胺对映体

金京玉1*, 黃虎2, 李元宰2*   

  1. 1. 浙江普洛家园药业有限公司, 浙江 东阳 322118; 2. 朝鲜大学药科大学, 韩国光州广域市501-759
  • 收稿日期:2010-12-15 修回日期:2011-02-28 出版日期:2011-04-28 发布日期:2011-04-28
  • 通讯作者: 李元宰,博士,教授,主要研究方向为手性药物分析. E-mail: wlee@chosun.ac.kr.金京玉,博士,研究员. E-mail: jinjingyu2002@yahoo.com.cn.

Enantiomer separation of α-amino acid methyl esters and some aliphatic amines as 9-anthraldimine derivatives by high performance liquid chromatography

JIN Jingyu1*, HUANG Hu2, LEE Wonjae2*   

  1. 1. Zhejiang Apeloa Jiayuan Pharmaceutical Co., Ltd., Dongyang 322118, China; 2. College of Pharmacy, Chosun University, Gwangju 501-759, Republic of Korea
  • Received:2010-12-15 Revised:2011-02-28 Online:2011-04-28 Published:2011-04-28

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644

被引次数

4

摘要： 采用高效液相色谱法,以9-蒽醛为衍生试剂,在5种多糖衍生物的手性固定相(CSPs)上对几种α-氨基酸甲酯对映体进行了手性分离。色谱条件如下: 流动相为含3%～10%(v/v)异丙醇的正己烷溶液,流速为1.0 mL/min,检测波长为254 nm。结果表明,α-氨基酸甲酯-9-蒽醛亚胺衍生物在Chiralcel OD柱或Chiralcel OD-H柱上的手性分离结果优于其他CSPs,而且在Chiralcel OD柱或Chiralcel OD-H柱上全部得到了基线拆分(α=1.24～5.47, Rs=2.56～13.90), L-对映体在这两种色谱柱上的保留强于D-对映体。同时还考察了几种脂肪胺在5种多糖衍生物手性固定相上的对映体拆分效果,结果表明脂肪胺的9-蒽醛亚胺衍生物在Chiralcel OD柱或Chiralcel OD-H柱上的分离效果良好。该法可用于其他α-氨基酸酯和胺类化合物对映体的分析。

关键词: 9-蒽醛亚胺衍生物, 氨基酸甲酯, 对映体拆分, 高效液相色谱法, 手性固定相

Abstract: The liquid chromatographic enantiomer separation of several α-amino acid methyl esters as 9-anthraldehyde Schiff base derivatives on five polysaccharide-derived chiral stationary phases (CSPs) was described. The 9-anthraldehyde imine derivatives of α-amino acid esters were prepared by stirring 9-anthraldehyde with the α-amino acid ester hydrochloride salts. The chromatographic conditions were 3%~10% (v/v) 2-propanol-n-hexane as the mobile phases at the flow rate of 1.0 mL/min and detected at UV 254 nm. The performance of Chiralcel OD (or Chiralcel OD-H) among the five CSPs was superior to those of the other CSPs for the resolution of 9-anthraldimine derivatives of α-amino acid methyl esters. The enantiomers of all α-amino acid methyl esters as the 9-anthraldimine derivatives were base-line resolved on Chiralcel OD or Chiralcel OD-H (α=1.24~5.47, Rs=2.56~13.90). The L-enantiomers of all analytes were strongerly restrained than the respective D-enantiomers on the Chiralcel OD (or Chiralcel OD-H) CSPs. The method was also used for the enantiomer separation of aliphatic amines and good separation was obtained. It is expected that the analytical method will be useful for the enantiomer resolution of other α-amino acid esters and amine compounds as 9-anthraldimine derivatives.

Key words: 9-anthraldimine derivative, chiral stationary phase (CSP), enantiomer separation, α-amino acid methyl ester, high performance liquid chromatography (HPLC)