Related Experiment Video
Updated: Aug 28, 2025

Methods to Identify the NMR Resonances of the 13C-Dimethyl N-terminal Amine on Reductively Methylated Proteins
Published on: December 12, 2013
Proton transfer mediated recognition of amines by ionizable macrocyclic receptors
Giuseppe Gattuso1, Daniele Crisafulli1, Marco Milone1
1Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, Università degli Studi di Messina, Viale F. Stagno d'Alcontres, 31, 98166 Messina, Italy. ggattuso@unime.it.
Abstract:
Ammonium ion/carboxylate ion pairing is a key interaction ubiquitous in biological systems, but amine recognition by ionizable molecular receptors, mediated by host-to-guest proton transfer, has too often been overlooked as a design element for molecular recognition. This survey will show that proton transfer mediated recognition is a powerful and versatile tool that can be made to work with different amines and diverse macrocyclic scaffolds, such as crown ethers, calixarenes or pillararenes. We will trace the history of this recognition motif since Cram's first report half a century ago down to the latest applications in supramolecular sensing, drug-delivery and materials science, highlighting along the way the impact of host-to-guest proton transfer on self-assembly and molecular recognition.
Related Concept Videos
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
NMR Spectroscopy Of Amines
Preparation of Amines: Reductive Amination of Aldehydes and Ketones
Basicity of Heterocyclic Aromatic Amines
Structure of Amines
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

