Nuclear magnetic resonance characterization of 6 alpha-chloro-5 beta-cholestane-3 beta,5-diol formed from the reaction of hypochlorous acid with cholesterol

被引：21

作者：

Carr, AC ^{[1
]}

Winterbourn, CC ^{[1
]}

Blunt, JW ^{[1
]}

Phillips, AJ ^{[1
]}

Abell, AD ^{[1
]}

机构：

[1] UNIV CANTERBURY,DEPT CHEM,CHRISTCHURCH 1,NEW ZEALAND

来源：

LIPIDS | 1997年 / 32卷 / 04期

关键词：

D O I：

10.1007/s11745-997-0046-8

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：

Hypochlorous acid generated by neutrophil myeloperoxidase has been shown to convert cholesterol into three different chlorohydrin isomers which previously had not been fully characterized. We have reacted hypochlorous acid with cholesterol/1,2-dipalmitoyl phosphatidylcholine liposomes to give these three major products and established that they are 6 beta-chloro-5 alpha-cholestane-3 beta,5-diol (chlorohydrin 1), 5 alpha-chloro-6 beta-cholestane-3 beta,6-diol (chlorohydrin 2) and 6 alpha-chloro-5 beta-cholestane-3 beta,5 -diol (chlorohydrin 3). These products were separated by thin-layer chromatography and fully characterized by H-1, C-13, attached proton test, doublequantum correlation spectroscopy, total correlation spectroscopy, heteronuclear multiple bond correlation and heteronuclear multiple quantum coherence nuclear magnetic resonance spectroscopy.

引用

页码：363 / 367

页数：5

共 18 条

[1] BIOLOGICAL REACTIVITY OF HYPOCHLOROUS ACID - IMPLICATIONS FOR MICROBICIDAL MECHANISMS OF LEUKOCYTE MYELOPEROXIDASE [J].