Chiral α-substituted α-aryloxy acetic acids: Synthesis,absolute configuration,chemical resolution,and direct separation by hplc |
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Authors: | G Bettoni S Ferorelli F Loiodice N Tangari V Tortorella F Gasparrini D Misiti C Villani |
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Abstract: | Several α-monoalkyl-α-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. © 1992 Wiley-Liss, Inc. |
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Keywords: | enantiomers chiral phase chiral recognition aryloxyacetic acids optical rotatory dispersion circular dichroism biological stereospecificity myotonia |
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