Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels–Alder Reactions. Issue 49 (3rd November 2017)

• Record Type: Journal Article
• Authors: Palma, Aniello; Artelsmair, Markus; Wu, Guanglu; Lu, Xiaoyong; Barrow, Steven J.; Uddin, Najib; Rosta, Edina; Masson, Eric; Scherman, Oren A.
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 49(2017)
• Page Start: 15688
• Page End: 15692
• Publication Date: 2017-11-03
• Subjects: biomimetic catalysts -- cucurbit[7]uril -- Diels–Alder reactions -- enzyme mimics; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201706487
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Copycat .: Cucurbit[7]uril (CB[7]) is able to catalyse Diels–Alder reactions for substituted and otherwise unreactive N ‐allyl‐2‐furfurylamines, thus imitating the role of a Diels–Alderase enzyme. Despite the reaction products exhibiting higher binding affinities for CB[7] than their reactants, Diels–Alder reactions can indeed proceed under mild and biomimetic catalytic conditions.