Formation of cyclopentenones from all-(E) hydroperoxides of linoleic acid via allene oxides.: New insight into the mechanism of cyclization

被引：16

作者：

Grechkin, AN

Hamberg, M

机构：

[1] Russian Acad Sci, Inst Biochem & Biophys, Kazan 420503, Russia

[2] Karolinska Inst, Dept Med Biochem & Biophys, Dept Physiol Chem 2, Stockholm, Sweden

来源：

FEBS LETTERS | 2000年 / 466卷 / 01期

基金：

俄罗斯基础研究基金会;

关键词：

linoleic acid hydroperoxide; allene oxide synthase; cyclization mechanism; cyclopentenone formation; oxylipin;

D O I：

10.1016/S0014-5793(99)01759-7

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：

Conversions of (Z,E)- and (E,E)-isomers of linoleic acid 13- and 9-hydroperoxides with flax and maize alkene oxide synthase were studied. All-(E) but not (Z,E) hydroperoxides readily undergo cyclization via allene oxides into trans-cyclopentenones. These results suggest that double bond geometry dramatically affects the formation of pericyclic pentadienyl cation intermediate and thus the capability of 18:2-allene oxides to undergo electrocyclization into cyclopentenones. (C) 2000 Federation of European Biochemical Societies.

引用

收藏

页码：63 / 66

页数：4

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