University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom.
J Am Chem Soc. 2011 Mar 23;133(11):3804-7. doi: 10.1021/ja200130h. Epub 2011 Feb 28.
We describe the use of dynamic combinatorial chemistry to discover a new series of linear hydrazone-based receptors that bind multiple dihydrogen phosphate ions. Through the use of a template-driven, selection-based approach to receptor synthesis, dynamic combinatorial chemistry allows for the identification of unexpected host structures and binding motifs. Notably, we observed the unprecedented selection of these linear receptors in preference to competing macrocyclic hosts. Furthermore, linear receptors containing up to nine building blocks and three different building blocks were amplified in the dynamic combinatorial library. The receptors were formed using a dihydrazide building block based on an amino acid-disubstituted ferrocene scaffold. A detailed study of the linear pentamer revealed that it forms a helical ditopic receptor that employs four acylhydrazone hydrogen-bond donor motifs to cooperatively bind two dihydrogen phosphate ions.
我们描述了使用动态组合化学来发现一系列新的基于线性腙的受体，这些受体可以结合多个二氢磷酸盐离子。通过使用模板驱动、基于选择的受体合成方法，动态组合化学允许鉴定出意想不到的主体结构和结合基序。值得注意的是，我们观察到这些线性受体的选择出乎意料，而不是竞争的大环主体。此外，在动态组合文库中，含有多达九个构建块和三个不同构建块的线性受体被放大。受体是由基于氨基酸取代二茂铁支架的二酰肼构建块形成的。对线性五聚体的详细研究表明，它形成了一个螺旋双位点受体，它采用四个酰腙氢键供体基序来协同结合两个二氢磷酸盐离子。
