A GAS-LIQUID-CHROMATOGRAPHIC METHOD FOR STERIC ANALYSIS OF 2-HYDROXY, 3-HYDROXY, AND 2,3-DIHYDROXY ACIDS

被引：8
|
作者：
ZHANG, LY [1 ]
HAMBERG, M [1 ]
机构：
[1] KAROLINSKA INST,DEPT MED BIOCHEM & BIOPHYS,DIV PHYSIOL CHEM 2,S-17177 STOCKHOLM,SWEDEN
来源：
CHEMISTRY AND PHYSICS OF LIPIDS | 1994年 / 74卷 / 02期
关键词：
HYDROXY ACID; PHENYLALANINE; STERIC ANALYSIS; GAS-LIQUID CHROMATOGRAPHY;
D O I：
10.1016/0009-3084(94)90056-6
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A method was developed for assignment of the absolute configuration of oxylipin-derived 2-hydroxy acids, 3-hydroxy acids and 2,3-dihydroxy acids. The monohydroxy acids were converted into diastereomeric N-(propionoxyacyl)-L-phenylalanine-methyl ester (PAP) derivatives by coupling to the methyl ester of L-phenylalanine followed by propionylation, whereas the 2,3-dihydroxy acids were derivatized by treatment with L-phenylalanine methyl ester followed by acetone and perchloric acid, to afford diastereomeric N-(2,3-isopropylidenedioxyacyl)-L-phenyl methyl ester (IAP) derivatives. The PAP and IAP derivatives were readily resolved by capillary gas-liquid chromatography. In addition, the method described allowed steric analysis of 3-hydroxy-3-methylheptanoic acid, a branched chain hydroxy acid derived from the prostaglandin analogue, misoprostol.
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页码：151 / 161
页数：11
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