Fahlstadius P, Hamberg M
Department of Physiological Chemistry, Karolinska Institutet, Stockholm, Sweden.
Chem Phys Lipids. 1989 Jul;51(1):15-22. doi: 10.1016/0009-3084(89)90061-3.
A gas-liquid chromatographic method for determination of the absolute configuration of the two chiral carbon atoms of epoxy fatty acids was developed. The method involved (1) conversion of the saturated epoxy ester into a pair of regioisomeric allylic alcohols by consecutive treatments with selenophenoxide anion and hydrogen peroxide, (2) oxidative ozonolysis performed on the (-)-menthoxycarbonyl derivatives of the allylic alcohols, and (3) steric analysis of the resulting two 2-hydroxy acids (methyl esters, (-)-menthoxycarbonyl derivatives) by gas-liquid chromatography using appropriate reference compounds. Application of the method for steric analysis of several synthetic epoxyoctadecanoates as well as (+)-vernolic acid derived from Vernonia galamensis is described.
建立了一种气相色谱法，用于测定环氧脂肪酸两个手性碳原子的绝对构型。该方法包括：（1）通过用苯硒酚阴离子和过氧化氢连续处理，将饱和环氧酯转化为一对区域异构体烯丙醇；（2）对烯丙醇的（-）-薄荷氧基羰基衍生物进行氧化臭氧分解；（3）使用合适的参考化合物，通过气相色谱对生成的两种2-羟基酸（甲酯，（-）-薄荷氧基羰基衍生物）进行立体分析。描述了该方法在几种合成环氧十八烷酸酯以及来自加拉曼菊的（+）-斑鸠菊酸的立体分析中的应用。
