NDLI: Guest Covalent Capture by a Host: A Biomimetic Strategy for the Selective Functionalization of a Cavity

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Guest Covalent Capture by a Host: A Biomimetic Strategy for the Selective Functionalization of a Cavity

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Guest Covalent Capture by a Host: A Biomimetic Strategy for the Selective Functionalization of a Cavity

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Menard, Nicolas Reinaud, Olivia Colasson, Benoit
Description	Author Affiliation: Menard N ( Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, PRES Sorbonne Paris Cité, 45 rue des Saints Pères, 75006 Paris, France.)
Abstract	A biomimetic strategy for the monofunctionalization of a calix[6]arene core is described. It is based on host–guest chemistry (mimicking the Michaelis–Menten adduct in enzymes) and allows the finely tuned pre-organization of the substrate (an alkyne) with respect to the reactant (three azido groups introduced at the calixarene large rim). It is shown that the thermal Huisgen reaction implemented in this work proceeds under very mild conditions with total regioselectivity of the cycloaddition process. The scope of the reaction was explored and the results suggest that such a supramolecular strategy is quite versatile and could be applied to the selective functionalization of other cavitands bearing different recognition patterns. A detailed structural, thermodynamic, and kinetic study is also reported, highlighting interesting biomimetic features: The importance of the host–guest adduct strength, the high sensitivity of the reaction to the pre-organization of the reactive partners (alkyne vs. azide), and a significant impact of the embedment on the transition state. The self-coordination of the monofunctionalized products was also studied and an “endo/exo” switch of the internal side-chain could be triggered by adding competitive ligands.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	2
Volume Number	19
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2013-01-07
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Biomimetics Calixarenes Chemistry Phenols Acetylene Alcohols Amines Click Chemistry Models, Molecular Molecular Conformation Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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