NMR SHIFT METHOD FOR DETERMINATION OF THE ENANTIOMERIC COMPOSITION OF HYDROPEROXIDES FORMED BY LIPOXYGENASE

被引：40

作者：

VANOS, CPA

VENTE, M

VLIEGENTHART, JFG

机构：

[1] Laboratory of Organic Chemistry, State University Utrecht, Croesestraat 79

来源：

BIOCHIMICA ET BIOPHYSICA ACTA | 1979年 / 574卷 / 01期

关键词：

Enantiomer composition; Hydroperoxide; Lipoxygenase;

D O I：

10.1016/0005-2760(79)90089-4

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 is presented for determination of the enantiomeric composition of hydroxyperoxides formed by enzymic oxygenation of unsaturated fatty acids. After reduction of the hydroperoxy group with NaBH4, and esterification, the positional isomers of the resulting hydroxy compounds are separated by high performance liquid chromatography. The latter are subsequently subjected to a chiral derivatization to form diastereomeric α-methoxy-α-trifluoromethylphenylacetate esters. Determination of the diastereomeric composition by a NMR shift experiment furnishes the enantiomeric composition of the parent hydroperoxides. The method has been applied to the hydroperoxides formed by incubation of linoleic acid by corn germ or soybean lipoxygenase. Our results indicate that under the conditions used the hydroperoxides are mainly enantiospecifically formed. © 1979.

引用

页码：103 / 111

页数：9

共 14 条

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