Complexes Formed between Artificial Receptors and β‐Glucopyranoside in the Crystalline State

• Published in: European journal of organic chemistry 2020-12, Vol.2020 (45), p.7023-7034
• Main Authors: Köhler, Linda, Seichter, Wilhelm, Mazik, Monika
• Format: Article
• Language: English
• Subjects: Binding; Carbohydrates; CH‐π Interactions; Crystal structure; Crystallinity; Feature recognition; Hydrogen bonds; Molecular recognition; Proteins; Receptors; Receptor‐sugar complexes; Sugar
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202001101

In contrast to numerous known crystal structures of protein‐carbohydrate complexes, which act as a source of structural information about carbohydrate‐mediated recognition processes, there are only individual literature reports on crystal structures of complexes formed between artificial receptors and sugars. In this context, the new crystalline complexes of acyclic receptors and β‐d‐glucopyranoside described in this article provide particularly valuable model systems to study the basic molecular features of carbohydrate recognition. The detailed analyses of the binding modes observed in these complexes have shown their remarkable similarity to those used by carbohydrate‐binding proteins. It is noteworthy that many of the basic molecular features of protein‐carbohydrate interactions, that have been summarized years ago in some literature reports, apply to interactions observed in complexes formed by the artificial receptors. Detailed analyses of the binding modes observed in the crystalline complexes of artificial receptors and β‐glucopyranoside provide deeper insights into the phenomena of molecular recognition of carbohydrates and show their remarkable similarity to those used by carbohydrate‐binding proteins. Remarkably, each of the three crystal structures discussed in this paper is characterized by the presence of two types of receptor‐sugar complexes.