SUPERCRITICAL-FLUID CHROMATOGRAPHIC-SEPARATION OF BETA-BLOCKERS ON CHYROSINE-A - INVESTIGATION OF THE CHIRAL RECOGNITION MECHANISM USING MOLECULAR MODELING

被引：29

作者：

BARGMANNLEYDER, N ^{[1
]}

SELLA, C ^{[1
]}

BAUER, D ^{[1
]}

TAMBUTE, A ^{[1
]}

CAUDE, M ^{[1
]}

机构：

[1] ECOLE SUPER PHYS & CHIM IND VILLE PARIS,CHIM ANALYT LAB,CNRS,UNITE RECH 437,F-75231 PARIS 05,FRANCE

来源：

ANALYTICAL CHEMISTRY | 1995年 / 67卷 / 05期

关键词：

D O I：

10.1021/ac00101a024

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

Using supercritical fluid chromatography (SFC), the direct separation of a series of beta-blockers has been carried out on the commercially available ChyRoSine-A and on its improved version. Surprisingly, these solutes appeared to be poorly resolved using normal phase liquid chromatography (NPLC). The chromatographic behaviors (both in SFC and NPLC) of various analogues of propranolol have been studied, and further spectroscopic investigations have been carried out, Starting from these data, a detailed chiral recognition mechanism has been elaborated based on molecular modeling, It appeared that the solvating effect of carbon dioxide induces a change of the propranolol conformations that is geometrically favorable to the chiral discrimination, this change of conformation occurs in the presence of carbon dioxide only if the solute bears both an amino proton and an ether function separated the one from the other by three carbon atoms.

引用

页码：952 / 958

页数：7

共 28 条

[1]

Ariens EJ, 1989, CHIRAL SEPARATIONS H, P31

[2] A NEW APPROACH FOR THE DIRECT RESOLUTION OF RACEMIC BETA-ADRENERGIC BLOCKING-AGENTS BY HPLC [J].