Synthesis of a derivative of racemic 3-hydroxy-2,4,6-trimethyltetracosanoic (mycolipanolic) acid and racemic 2,4,6-trimethyltetracos-2-enoic (mycolipenic) acid

被引：4

作者：

Wallace, PA ^{[1
]}

Minnikin, DE ^{[1
]}

机构：

[1] UNIV NEWCASTLE,DEPT CHEM,NEWCASTLE TYNE NE1 7RU,TYNE & WEAR,ENGLAND

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 1996年 / 83卷 / 01期

基金：

英国工程与自然科学研究理事会;

关键词：

Mycobacterium tuberculosis; mycolipanolic acid; mycolipenic acid; acyl-alpha; alpha'-trehaloses; glycolipid antigens;

D O I：

10.1016/0009-3084(96)02571-6

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：

Racemic 2,4-dimethyldocosanol, available from previous studies, was oxidised to the aldehyde using pyridinium chlorochromate. Aldol reaction of 2,4-dimethyldocosanal with methyl propionate afforded racemic methyl 3-hydroxy-2,4,6-trimethyltetracosanoic acid. The hydroxy function was protected as a tert-butyldimethylsilyl ether and the ester functionality hydrolysed to the free acid. Wittig reaction of 2,4-dimethyldocosanal using 1-carboethoxyethylidenetriphenylphosphorane afforded the (E)-stereoisomer following removal of the small quantities of (Z)-isomer by column chromatography. The ethyl ester was hydrolysed to afford racemic 2,4,6-trimethyltetracos-2-enoic acid. These unusual fatty acids are characteristic of Mycobacterium tuberculosis.

引用

页码：1 / 8

页数：8

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