High-affinity anion binding by steroidal squaramide receptors.

High-affinity anion binding by steroidal squaramide receptors.
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类固醇方酰胺受体的高亲和力阴离子结合。

DOI:
10.1002/anie.201411805
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发表时间:
2015-04-07
影响因子:
16.6
通讯作者:
Davis, Anthony P.
Davis, Anthony P.
中科院分区:
化学1区
文献类型:
--
作者:
Edwards, Sophie J.;Valkenier, Hennie;Busschaert, Nathalie;Gale, Philip A.;Davis, Anthony P.

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通过将方酰胺基团置于甾体框架上的轴向位置,已经构建了非常强大的阴离子受体。类固醇预组织方酰胺NH基团,使得它们可以协同作用于结合阴离子,同时保持在非极性介质中的溶解度。酸性NH基团赋予比先前使用的脲或硫脲更高的亲和力。在氯仿中,四乙基铵盐的结合常数超过了1014 m−1,这是通过采用一种变化的克拉姆萃取方法测得的。受体也被研究为单层囊泡中的跨膜阴离子载体。不寻常的是,它们的活性与阴离子亲和力不相关,从而表明在阴离子载体的设计中结合强度的上限。
Exceptionally powerful anion receptors have been constructed by placing squaramide groups in axial positions on a steroidal framework. The steroid preorganizes the squaramide NH groups such that they can act cooperatively on a bound anion, while maintaining solubility in nonpolar media. The acidic NH groups confer higher affinities than previously-used ureas or thioureas. Binding constants exceeding 1014 m−1 have been measured for tetraethylammonium salts in chloroform by employing a variation of Cram’s extraction procedure. The receptors have also been studied as transmembrane anion carriers in unilamellar vesicles. Unusually their activities do not correlate with anion affinities, thus suggesting an upper limit for binding strength in the design of anion carriers.
DOI: 10.1039/c4sc01629g
发表时间: 2014-09-01
期刊: Chemical science
影响因子: 8.4
作者:
Busschaert N;Elmes RB;Czech DD;Wu X;Kirby IL;Peck EM;Hendzel KD;Shaw SK;Chan B;Smith BD;Jolliffe KA;Gale PA
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