硼酸功能化、分子印迹交联胶束对 d-aldose 在水中的选择性识别。
Selective Recognition of d-Aldohexoses in Water by Boronic Acid-Functionalized, Molecularly Imprinted Cross-Linked Micelles.
机构信息
Department of Chemistry, Iowa State University , Ames, Iowa 50011-3111, United States.
出版信息
J Am Chem Soc. 2016 Aug 10;138(31):9759-62. doi: 10.1021/jacs.6b04613. Epub 2016 Jul 27.
Abstract
Molecular imprinting within cross-linked micelles using 4-vinylphenylboronate derivatives of carbohydrates provided water-soluble nanoparticle receptors selective for the carbohydrate templates. Complete differentiation of d-aldohexoses could be achieved by these receptors if a single inversion of hydroxyl occurred at C2 or C4 of the sugar or if two or more inversions took place. Glycosides with a hydrophobic aglycan displayed stronger binding due to increased hydrophobic interactions.
摘要
利用碳水化合物的 4-乙烯基苯硼酸衍生物在交联胶束内进行分子印迹，为碳水化合物模板提供了对水可溶性纳米颗粒受体的选择性。如果糖的 C2 或 C4 位发生单个羟基反转，或者发生两个或更多反转，则这些受体可以实现 d-醛糖的完全区分。由于疏水性糖苷配基增加了疏水性相互作用，因此具有疏水性糖苷配基的糖苷显示出更强的结合能力。
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2
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Langmuir. 2016 Jun 14;32(23):5703-13. doi: 10.1021/acs.langmuir.6b01162. Epub 2016 Jun 1.
3
Molecularly Responsive Binding through Co-occupation of Binding Space: A Lock-Key Story.通过共同占据结合空间实现分子响应性结合：一个锁钥故事。
Org Lett. 2016 Apr 1;18(7):1650-3. doi: 10.1021/acs.orglett.6b00527. Epub 2016 Mar 22.
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