Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels-Alder Reactions
Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels-Alder Reactions
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DOI：
10.1002/anie.201706487
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发表时间：
2017-12-04
影响因子：
16.6
通讯作者：
Scherman, Oren A.
中科院分区：
文献类型：
--
作者：
Palma, Aniello;Artelsmair, Markus;Scherman, Oren A.
使用超分子结构（人工酶）模拟天然酶活性的能力是一个充满活力的科学研究领域。在此，我们证明了葫芦[7]脲（CB[7]）可以在仿生条件下催化许多取代和非反应性N-烯丙基-2-糠胺的Diels-Alder反应，而不需要保护基团，在以前未报道的温和条件下产生强大的双离子。CB[7]将底物重新排列成高度反应性的构象，并将其与水性环境隔离，从而模仿天然狄尔斯-阿尔德酶的作用模式。这些发现可以直接应用于天然Diels-Alderase酶中观察到的产物抑制现象，并为开发新型超分子绿色催化剂铺平了道路。
The ability to mimic the activity of natural enzymes using supramolecular constructs (artificial enzymes) is a vibrant scientific research field. Herein, we demonstrate that cucurbit[7]uril (CB[7]) can catalyse Diels-Alder reactions for a number of substituted and unreactive N-allyl-2-furfurylamines under biomimetic conditions, without the need for protecting groups, yielding powerful synthons in previously unreported mild conditions. CB[7] rearranges the substrate in a highly reactive conformation and shields it from the aqueous environment, thereby mimicking the mode of action of a natural Diels-Alderase. These findings can be directly applied to the phenomenon of product inhibition observed in natural Diels-Alderase enzymes, and pave the way toward the development of novel, supramolecular-based green catalysts.