CHIRAL ALPHA-SUBSTITUTED ALPHA-ARYLOXY ACETIC-ACIDS - SYNTHESIS, ABSOLUTE-CONFIGURATION, CHEMICAL RESOLUTION, AND DIRECT SEPARATION BY HPLC

被引：48

作者：

BETTONI, G ^{[1
]}

FERORELLI, S ^{[1
]}

LOIODICE, F ^{[1
]}

TANGARI, N ^{[1
]}

TORTORELLA, V ^{[1
]}

GASPARRINI, F ^{[1
]}

MISITI, D ^{[1
]}

VILLANI, C ^{[1
]}

机构：

[1] UNIV ROME LA SAPIENZA, DIPARTIMENTO STUDI CHIM & TECNOL SOSTANZE BIOLOGIC, I-00185 ROME, ITALY

来源：

CHIRALITY | 1992年 / 4卷 / 03期

关键词：

ENANTIOMERS; CHIRAL PHASE; CHIRAL RECOGNITION; ARYLOXYACETIC ACIDS; OPTICAL ROTATORY DISPERSION; CIRCULAR DICHROISM; BIOLOGICAL STEREOSPECIFICITY; MYOTONIA;

D O I：

10.1002/chir.530040311

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Several alpha-monoalkyl-alpha-aryloxyacetic acids have been synthesized and resolved into their optical antipodes; their absolute configuration was also established by chiroptical and chemical methods. The two enantiomers of a series of these compounds show opposite effects on skeletal muscle fibers chloride conductance. Therefore a HPLC procedure was developed for the direct determination of the optical purity of the antipodes before submitting them to biological tests. The chromatographic study was performed on DACH-DNB chiral stationary phase which shows a remarkable enantioselectivity for the considered compounds as free acids, esters and amides under different conditions with essentially the same chiral mechanism of separation.

引用

页码：193 / 203

页数：11

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