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含羟基脂质与氢氧化三甲基锍的反应:O-甲基衍生物的形成

Reaction of lipids containing hydroxy groups with trimethylsulfonium hydroxide: formation of O-methyl derivatives.

作者信息

Vosmann K, Schulte E, Klein E, Weber N

机构信息

Institut für Chemie und Physik der Fette, BAGKF, Münster, Germany.

出版信息

Lipids. 1996 Mar;31(3):349-52. doi: 10.1007/BF02529884.

DOI:10.1007/BF02529884
PMID:8900467
Abstract

Base-catalyzed transesterification of acyl lipids with trimethylsulfonium hydroxide (TMSH) is an easy and convenient method for the preparation of fatty acid methyl esters (FAME) for gas chromatography (GC) analyses. We have found, however, that lipids containing hydroxy groups are partially converted to the corresponding O-methyl ether derivatives which may interfere with FAME in GC separations. For example, long-chain alcohols are found to be converted to alkyl methyl ethers, rac-1-O-alkylglycerols to the corresponding 2-O- and 3-O-monomethyl ethers, as well as 2,3-di-O-methyl ethers, hydroxy fatty acids to methoxy FAME, and cholesterol to cholesteryl 3 beta-methyl ether. From our results, it is obvious that TMSH derivatization method is not recommended without limitation for lipids containing hydroxy groups; it may be, however, of some diagnostic value for the analysis of such lipids by GC/mass spectrometry.

摘要

用氢氧化三甲锍(TMSH)进行的碱基催化酰基脂质酯交换反应是一种简便易行的制备用于气相色谱(GC)分析的脂肪酸甲酯(FAME)的方法。然而,我们发现,含羟基的脂质会部分转化为相应的O-甲基醚衍生物,这可能会在GC分离中干扰FAME。例如,发现长链醇会转化为烷基甲基醚,外消旋1-O-烷基甘油会转化为相应的2-O-和3-O-单甲基醚以及2,3-二-O-甲基醚,羟基脂肪酸会转化为甲氧基FAME,胆固醇会转化为胆固醇3β-甲基醚。从我们的结果来看,很明显,对于含羟基的脂质,TMSH衍生化方法并非毫无限制地推荐使用;然而,它对于通过GC/质谱分析此类脂质可能具有一定的诊断价值。

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引用本文的文献

1
S-methyl derivatives from thiol compounds by the pyrolytic reaction with trimethylsulfonium hydroxide.通过与氢氧化三甲基锍的热解反应由硫醇化合物得到的S-甲基衍生物。
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本文引用的文献

1
Mass spectrometry in lipid research.脂质研究中的质谱分析。
J Lipid Res. 1960 Oct;1:361-90.