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Current Medicinal Chemistry


ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

Review Article

Aromatic Interactions in Glycochemistry: From Molecular Recognition to Catalysis

Author(s): Andrés González Santana, Laura Díaz-Casado, Laura Montalvillo, Ester Jiménez-Moreno, Enrique Mann and Juan Luis Asensio*

Volume 29, Issue 7, 2022

Published on: 09 July, 2021

Page: [1208 - 1218] Pages: 11

DOI: 10.2174/0929867328666210709120216

Price: $65


Aromatic platforms are ubiquitous recognition motifs occurring in protein carbohydrate- binding domains (CBDs), RNA receptors and enzymes. They stabilize the glycoside/ receptor complexes by participating in stacking CH/π interactions with either the α- or β- face of the corresponding pyranose units. In addition, the role played by aromatic units in the stabilization of glycoside cationic transition states has started being recognized in recent years. Extensive studies carried out during the last decade have allowed the dissection of the main contributing forces that stabilize the carbohydrate/aromatic complexes, while helping delineate not only the standing relationship between the glycoside/ aromatic chemical structures and the strength of this interaction but also their potential influence on glycoside reactivity.

Keywords: Carbohydrate recognition, stacking CH/π interactions, cation/π interactions, structure-stability relationships, glycosidic bond formation, carbohydrate-binding domains.

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