A convergent synthesis of core 2 branched sialylated and sulfated oligosaccharides.
A convergent synthesis of core 2 branched sialylated and sulfated oligosaccharides.
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核心 2 支链唾液酸化和硫酸化寡糖的聚合合成。
DOI：
10.1016/s0968-0896(02)00246-8
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发表时间：
2002
影响因子：
3.5
通讯作者：
Matta,KhushiL
中科院分区：
文献类型：
--
作者：
Xia,Jie;Alderfer,JamesL;Srikrishnan,Thamarapu;Chandrasekaran,EV;Matta,KhushiL
开发了用于合成核心2寡糖类似物1和2以及天然形式的唾液酸化和硫酸化六糖3的会聚途径。五糖24、27和六糖28的构建分别通过受体5、7和8中的6-OH的完全区域选择性糖基化来实现，这是由于在这些结构中伯羟基比仲轴羟基具有高得多的反应性。使用具有通过X射线晶体学分析建立的限定构型的供体10完成立体选择性唾液酸化。然后通过中间体24、27和29的系统脱保护获得目标寡糖1-3。获得这些目标寡糖1-3后，对这些分子作为酶底物进行生物学评价，并计划进行选择素结合研究。
A convergent pathway for the syntheses of core 2 oligosaccharide analogues 1 and 2, and a natural form sialylated and sulfated hexasaccharide 3 was developed. Construction of pentasaccharides 24, 27 and hexasaccharide 28 was achieved by complete regioselective glycosylation of the 6-OH in the acceptors 5, 7 and 8, respectively, owing to the much higher reactivity of the primary hydroxyl group over the secondary axial hydroxyl group in these structures. Stereoselective sialylation was accomplished using donor 10 with defined configuration established through X-ray crystallographic analysis. Target oligosaccharides 1–3 were then obtained by the systematic deprotection of intermediates 24, 27 and 29. With these target oligosaccharides 1–3 obtained, biological evaluations of these molecules as enzyme substrates was undertaken and selectin binding studies are planned.