Analogues of GM3 and GM2 gangliosides were chemoenzymatically synthesized on a multifunctional ceramide-type tether designed to facilitate diverse strategies for glycoconjugate synthesis. The truncated ceramide aglycon maintains the stereogenic centres of natural ceramide while avoiding extensive hydrophobicity that can hamper synthesis and purification of the glycolipids. Tetanus toxoid and BSA glycoconjugates of these two gangliosides were prepared for immunization of mice, and for solid phase assays to screen for ganglioside-specific antibodies. Inhibition experiments showed that antibodies generated by tetanus toxoid conjugates of GM3 and GM2 exhibited specificity for the carbohydrate epitope and the stereogenic centres of the ceramide.
通过
化学酶法,在多功能神经酰胺型接头上合成了GM3和GM2
神经节苷脂的类似物,该接头设计用于促进糖缀合物合成的多种策略。截短的神经酰胺非糖部分保留了天然神经酰胺的立体中心,同时避免了可能妨碍
糖脂合成和纯化的广泛疏
水性。为小鼠免疫接种和用于筛选
神经节苷脂特异性
抗体的固相测定准备了这两种
神经节苷脂与破伤风类毒素和
BSA的糖缀合物。抑制实验表明,通过GM3和GM2与破伤风类毒素结合物产生的
抗体对
碳水化合物表位和神经酰胺的立体中心表现出特异性。