Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels–Alder Reactions. (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. Volume 129:Number 49(2017)
• Page Start: 15894
• Page End: 15898
• Publication Date: 2017-11-03
• Subjects: Biomimetische Katalysatoren -- Cucurbit[7]uril -- Diels-Alder-Reaktionen -- Enzymmimetika; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201706487
• Languages: English
• ISSNs: 0044-8249

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.