原口动物门糖鞘脂的合成研究：节肢动物系列糖鞘脂的合成
Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids.
作者信息
Ohtsuka Isao, Hada Noriyasu, Sugita Mutsumi, Takeda Tadahiro
机构信息
Kyoritsu College of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
出版信息
Carbohydr Res. 2002 Nov 19;337(21-23):2037-47. doi: 10.1016/s0008-6215(02)00295-1.
Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar, have quite unique structures containing GlcNAcbeta-(1 --> 3)-Man and GalNAcbeta-(1 --> 4)-GlcNAcbeta-(1 --> 3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer and beta-D-GalNAcp-(1 --> 4)-beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages.
从绿蝇 Lucilia caesar 的幼虫中分离出的糖鞘脂具有相当独特的结构，包含 GlcNAcbeta-(1 --> 3)-Man 和 GalNAcbeta-(1 --> 4)-GlcNAcbeta-(1 --> 3)-Man。我们合成了两种糖鞘脂，即 beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer 和 beta-D-GalNAcp-(1 --> 4)-beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer。合成序列中的关键反应是应用分子内苷元传递（IAD）方法来合成 β-甘露吡喃糖苷键。
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