A Chiral Pyrrolic Tripodal Receptor Enantioselectively Recognizes β-Mannose and β-Mannosides
A Chiral Pyrrolic Tripodal Receptor Enantioselectively Recognizes β-Mannose and β-Mannosides
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DOI：
10.1002/chem.200902514
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发表时间：
2010-01-01
影响因子：
4.3
通讯作者：
Roelens, Stefano
中科院分区：
文献类型：
--
作者：
Arda, Ana;Venturi, Chiara;Roelens, Stefano
报道了一个新的手性受体家族的原型，该家族基于三足支架，并以含有反式-1，2-二氨基环己烷基序的吡咯结合臂为特征。设计了具有稍微扩大的空腔的笼，相信笼尺寸的微调将导致即使在更极性的介质中也显著改善的亲和力。三醛4与单-BOC保护的二胺2反应，然后还原所得席夫碱并随后脱保护氨基，得到三脚架六胺5，将其与吡咯-2，5-二甲醛在用于制备双环受体1的条件下缩合。初步筛选表明，虽然Glc，Gal和GlcNAc是中度结合的，但甘露糖苷发生了强烈的识别。在苯中也提取了β甘露糖，但程度较低（10%），α甘露糖未检出。
The prototype of a new family of chiral receptors based on a tripodal scaffold and featuring pyrrolic binding arms containing the trans-1,2- diaminocyclohexane motif, was reported. A cage endowed with a somewhat enlarged cavity was designed, in the belief that fine-tuning of the cage size would lead to a significantly improved affinity even in more polar media. Reaction of the trialdehyde 4 with the mono-BOC-protected diamine 2, followed by reduction of the resulting Schiff base and subsequent deprotection of the amino groups, yielded the tripodal hexaamine 5, which was condensed with pyrrole-2,5- dicarbaldehyde under the conditions used for preparing the bicyclic receptor 1. A preliminary screening indicated that, while Glc, Gal, and GlcNAc were moderately bound, strong recognition occurred with mannosides. βMannose was also extracted in benzene, though to a lesser extent (10%), and αMannose could not be detected.