Imprinted micelles for chiral recognition in water: shape, depth, and number of recognition sites
Imprinted micelles for chiral recognition in water: shape, depth, and number of recognition sites
复制标题
DOI：
10.1039/c7ob00764g
复制
发表时间：
2017-06-14
影响因子：
3.2
通讯作者：
Zhao, Yan
中科院分区：
文献类型：
--
作者：
Awino, Joseph K.;Zhao, Yan
手性分子识别在生物学、分离和不对称催化等领域具有重要意义。由于宿主和客体的手性之间没有直接的相关性，因此很难以合理的方式为手性客体设计分子受体。通过交联含有手性模板分子的表面活性剂胶束，我们获得了一些4-羟基脯氨酸衍生物的手性纳米颗粒受体。分子印迹使我们能够将手性信息直接从客体转移到宿主，使两者之间的分子识别具有高度可预测性。宿主和客体之间的疏水相互作用对这些化合物在水中的对映体和非对映体选择性分化有很大贡献，而发生在胶束表面附近的离子对相互作用的区别较小。手性识别可以通过调整绑定口袋的大小和形状来调节。
Chiral molecular recognition is important to biology, separation, and asymmetric catalysis. Because there is no direct correlation between the chiralities of the host and the guest, it is difficult to design a molecular receptor for a chiral guest in a rational manner. By cross-linking surfactant micelles containing chiral template molecules, we obtained chiral nanoparticle receptors for a number of 4-hydroxyproline derivatives. Molecular imprinting allowed us to transfer the chiral information directly from the guest to host, making the molecular recognition between the two highly predictable. Hydrophobic interactions between the host and the guest contributed strongly to the enantio-and diastereoselective differentiation of these compounds in water, whereas ion-pair interactions, which happened near the surface of the micelle, were less discriminating. The chiral recognition could be modulated by tuning the size and shape of the binding pockets.