通过叠氮鞘氨醇类似物全合成D-赤藓糖型鞘氨醇、N-棕榈酰鞘氨醇（神经酰胺）和葡糖神经酰胺（脑苷脂）。
The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog.
作者信息
Duclos R I
机构信息
Department of Physiology and Biophysics, Boston University School of Medicine, 715 Albany Street, 02118-2526, Boston, MA, USA.
出版信息
Chem Phys Lipids. 2001 Jun;111(2):111-38. doi: 10.1016/s0009-3084(01)00152-9.
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.
通过一种手性特异性方法从D-半乳糖出发，经叠氮鞘氨醇中间体完成了D-赤藓糖型鞘氨醇（9）的全合成，得到了高度均一（>99.9% C18:1）的鞘氨醇碱（9），该产物未观察到烯烃异构化副产物，并且通过一种利用莫舍尔酸的新方法证明其为光学纯。通过两种方法由这种鞘氨醇（9）与高度均一（99.8% C16:0）的棕榈酸制备了神经酰胺（10）。脑苷脂葡萄糖神经酰胺（23）是该系列中下一个以高度均一形式合成的鞘脂。这三种鞘脂目前正用于对其水合生物分子组装体结构的生物物理研究。
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