Synthesis of (5Z,8Z,11Z,14Z)-18-and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-3H8]-analogues through a common synthetic route

被引：7

作者：

Romanov, SG

Ivanov, IV

Shevchenko, VP

Nagaev, IY

Pushkov, AA

Myasoedov, NF

Myagkova, GI

Kuhn, H

机构：

[1] MV Lomonosov State Acad Fine Chem Technol, Moscow 119571, Russia

[2] Humboldt Univ, Clin Charite, Inst Biochem, D-10117 Berlin, Germany

[3] Inst Genet Mol, Moscow 123182, Russia

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 2004年 / 130卷 / 02期

基金：

俄罗斯基础研究基金会;

关键词：

eicosanoids; photo-affinity probes; cross-coupling; azido compounds; tritium-labelled fatty acids;

D O I：

10.1016/j.chemphyslip.2004.02.008

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：

Total synthesis of (5Z,8Z, 11Z, 14Z)-18- and 19-azidoeicosa-5,8,11,14-tetraenoic acids and their [5,6,8,9,11,12,14,15-H-3(8)]-analogues via the corresponding p-toluenesulphonates is reported. This synthetic approach allows the preparation of radioactively labelled arachidonic acid derivatives following a common synthetic route. Activity assays indicated that 15-lipoxygenases may tolerate the azido group in the substrate binding pocket and thus, radioactively labelled azido compounds may be used as photo-affinity probes to investigate mechanistic features of eicosanoid biosynthesis. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

引用

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页码：117 / 126

页数：10

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