The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog

被引：34

作者：

Duclos, RI ^{[1
]}

机构：

[1] Boston Univ, Sch Med, Dept Physiol & Biophys, Boston, MA 02118 USA

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 2001年 / 111卷 / 02期

基金：

美国国家卫生研究院;

关键词：

sphingosine; ceramide; cerebroside; glucosylceramide; azidosphingosine; Mosher's acid;

D O I：

10.1016/S0009-3084(01)00152-9

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：

The total synthesis of D-erythro-sphingosine (9) was performed by a chirospecific method starting from D-galactose via an azidosphingosine intermediate to give highly homogeneous (>99.9% C18:1) sphingosine base (9) which contained no observable olefin isomerization by product and was demonstrated to be optically pure by a novel method utilizing Mosher's acid. Ceramide (10) was prepared from this sphingosine (9) with highly homogeneous (99.8% C16:0) palmitic acid by two methods. The cerebroside glucosylceramide (23) was the next sphingolipid in this series to be synthesized in a highly homogeneous form. These three sphingolipids are currently being used for biophysical studies of the structures of their hydrated bio-molecular assemblies. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.

引用

页码：111 / 138

页数：28