Oligosaccharide synthesis by affinity separation based on molecular recognition between podand ether and ammonium ion
Oligosaccharide synthesis by affinity separation based on molecular recognition between podand ether and ammonium ion
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DOI：
10.1055/s-2005-872269
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发表时间：
2005-09-19
期刊：
影响因子：
2
通讯作者：
Kusumoto, S
中科院分区：
文献类型：
--
作者：
Fukase, K;Takashina, M;Kusumoto, S
我们之前报道了一种新的合成方法，称为“基于亲和分离的合成”（SAS），其中通过使用标签的特定分子识别的固相萃取从反应混合物中分离出所需的标记化合物。冠醚标签和聚合物负载的铵离子之间的相互作用最初用于SAS。本研究提出了一种利用豆荚型标签（伪苯并-31冠-10结构）合成低聚糖的SAS新方法。豆荚标签比相应的冠醚更容易合成。荚果部分通过适当的连接体附着在单糖残基上。将标记的单糖与糖基供体糖基化后，对反应混合物进行亲和分离。通过豆荚与铵离子之间的亲和关系，有效地分离了具有豆荚和标签的所需化合物。将微反应器与SAS系统集成的连续流合成技术应用于低聚糖的高通量合成。
We previously reported a new synthetic methodology termed 'synthesis based on affinity separation' (SAS) in which the desired tagged compound was separated from the reaction mixture by solid-phase extraction using specific molecular recognition of the tag. The interaction between a crown ether tag and polymer-supported ammonium ion was initially employed for SAS. In the present study, a new SAS method using a podand-type tag, a pseudo-benzo-31-crown-10 structure, was elaborated for oligosaccharide synthesis. The podand tag was much easier to synthesize than the corresponding crown ether. The podand moiety was attached to the monosaccharide residue via appropriate linkers. After glycosylation of the tagged monosaccharide with a glycosyl donor, the reaction mixture was subjected to the affinity separation. The desired compounds possessing the podand tag were effectively separated by the affinity between the podand and the ammonium ion. Continuous flow synthesis by integration of a microreactor and the present SAS system was applied for high throughput oligosaccharide synthesis.