Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine
Large scale synthesis of linker-modified sialyl LewisX, LewisX and N-acetyllactosamine
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DOI：
10.1016/s0040-4020(98)00294-4
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发表时间：
1998-06-04
期刊：
影响因子：
2.1
通讯作者：
Stahl, W
中科院分区：
文献类型：
--
作者：
Kretzschmar, G;Stahl, W
将唾液酸基-刘易斯（X）（1b）、刘易斯（X）（2）和N-乙酰基乳糖胺（3）的合成放大至克量，以获得足够的材料用于全面的药物评价和用于旨在获得更有效的选择素拮抗剂的衍生化。二糖3由廉价的乳糖合成，以提供通用的结构单元，用于刘易斯型寡糖的替代方法，或制备多价LacNAc模板以通过糖基转移酶反应进一步加工。所有合成都涉及合理的大规模程序，特别是通过最小化步骤的数量和在糖基化中使用重金属盐。(C)1998爱思唯尔科技有限公司版权所有。
The synthesis of sialyl-Lewis(X) (1b), Lewis(X) (2) and N-acetyllactosamine (3), each being attached to the 1 beta-O-(6-amino)hexyl handle, were scaled up to gram amounts to obtain sufficient material for thorough pharmaceutical evaluations and for derivatizations aiming at more potent selectin antagonists. The disaccharide 3 was synthesised from inexpensive lactose to provide a versatile building block, either to be used for alternative approaches to the Lewis type oligosaccharides, or to prepare polyvalent LacNAc templates to be further elaborated by glycosyltransferase reactions. All syntheses were directed to reasonable large scale procedures, especially by minimising the number of steps and the use of heavy metal salts in glycosylations. (C) 1998 Elsevier Science Ltd. All rights reserved.