色谱

色谱

• 研究简报 • 上一篇    下一篇

高效液相色谱法分离测定3-取代-(R,S)-β-丙氨酸对映异构体

陈衍强,邱孝苹,徐修容   

  1. Shanghai ACI Biotech Co. Ltd, Shanghai 200237, China
  • 收稿日期:2004-03-19 修回日期:1900-01-01 出版日期:2005-05-30 发布日期:1988-09-25
  • 通讯作者: 陈衍强
  • 基金资助:

Separation of 3-Substituted-(R,S)-β-Alanine　Derivatives by High Performance Liquid Chromatography

CHEN Yanqiang, QIU Xiaoping, XU Xiurong   

  1. Shanghai ACI Biotech Co. Ltd, Shanghai 200237, China
  • Received:2004-03-19 Revised:1900-01-01 Online:2005-05-30 Published:1988-09-25

PDF

654

被引次数

6

摘要： 以1-氟-2,4-二硝基-5-L-缬氨酰胺(Marfey试剂)为衍生试剂,采用反相高效液相色谱法分离了3-取代-(R,S)-β- 丙氨酸对映异构体。采用梯度洗脱(流动相 A:体积分数为0.1%的三氟乙酸乙腈溶液；流动相B:体积分数为0.1%的三氟乙 酸水溶液)成功分离了 32种3-取代-(R,S)-β-丙氨酸衍生物,所有化合物都是R型异构体衍生物(R-L)较S型异构体衍生物 (S-L)先洗脱。除3-羟基苯和4-羟基苯的疏水参数较小,但其取代的β-丙氨酸衍生物的保留时间较长、分离因子较小外, 其他疏水参数大的取代基的β-丙氨酸衍生物保留时间都长于疏水参数小的取代基的β-丙氨酸衍生物。该文同时测定了R -和S-β-丙氨酸的对映体过剩值。

关键词: 3-取代-(R,S)-β-丙氨酸衍生物, 对映体过剩值 , 对映异构体, 高效液相色谱法

Abstract: 3-Substituted-(R,S)-β-alanines derivatized by 1-fluoro-2,4-dinitro-5-L-valinamide (Marfey’s reagent) were successfully separated by reversed-phase high performance liquid chromatography. The separations were performed with gradient elution. The mobile phase A was acetonitrile containing 0.1%(v/v) trifluoroacetic acid and the mobile phase B was 0.1%(v/v) trifluoroacetic acid aqueous solution. Thirty-two pairs of 3-substituted-(R,S)-β-alanine derivatives, phenyl, substituted phenyl, naphthyl, substituted pyridyl and thienyl, were separated. The mobile phase A content was changed from 35% to 75% in 20 min. All (R-L)-diastereomers were eluted prior to the (S-L) ones. Substituents with larger hydrophobic parameters (π) gave longer retention times (tR) for their derivatives than those with smaller ones except for 3-hydroxyphenyl and 4-hydroxyphenyl substituents. The positioning of the substituents on benzene ring of β-alanines (β-Ala) also influenced tR and separation. 4-Subsituted-phenyl-(R,S)-β-Ala derivatives gave longer tR and better separation than 2-substituted isomers. The enantiomer excess values of R- and S-β-Ala were also determined.

Key words: , 3-substituted-(R,S)-β-alanine derivatives, high performance liquid chromatography