Low‐Symmetry Macrocycles and Cages for Carbohydrate Recognition
Open Access
- 20 July 2023
- journal article
- review article
- Published by Wiley in Chempluschem
- Vol. 88 (7) , e202300291
Abstract
The recognition of carbohydrate plays a key role in numerous biological processes. Thus, artificial receptors have been synthesized to mimic these biological systems. To date, most of the receptors reported for carbohydrate complexation present highly symmetrical cavities, probably because their syntheses require less synthetic efforts and are easier to achieve and control. However, carbohydrates display complex, asymmetrical structures suggesting that hosts with low symmetry might be more adapted to recognize these guests. Here, we described the strategies that have been used to complex carbohydrates with macrocycles and cages presenting low symmetry and the potential of this approach. Self‐assembled cages are first described, then covalent macrocycles and cages are presented and for each example the binding properties of low‐symmetry systems are compared to those of their higher‐symmetry counterparts.Keywords
This publication has 112 references indexed in Scilit:
- High‐Affinity Disaccharide Binding by Tricyclic Synthetic LectinsAngewandte Chemie International Edition, 2012
- Face-driven octanuclear cerium(iv) luminescence polyhedra: synthesis and luminescent sensing natural saccharidesChemical Communications, 2011
- Exclusive enantioselective recognition of glucopyranosides by inherently chiral hemicryptophanesChemical Communications, 2011
- A Self‐Assembled Pyrrolic Cage Receptor Specifically Recognizes β‐GlucopyranosidesAngewandte Chemie, 2006
- Carboxylate-Based Receptors for the Recognition of Carbohydrates in Organic and Aqueous MediaThe Journal of Organic Chemistry, 2006
- Carbohydrate–carbohydrate interactions in cell recognitionCurrent Opinion in Structural Biology, 2004
- Chemical Diversity in the Sialic Acids and Related α-Keto Acids: An Evolutionary PerspectiveChemical Reviews, 2002
- 129Xe and 1H NMR Study of the Reversible Trapping of Xenon by Cryptophane-A in Organic SolutionJournal of the American Chemical Society, 1998
- A New Family of Chiral Binaphthyl‐Derived Cyclophane Receptors: Complexation of PyranosidesAngewandte Chemie International Edition, 1995
- Eine neue Klasse chiraler, von 1,1′‐Binaphthyl abgeleiteter Cyclophan‐Rezeptoren: Komplexierung von PyranosidenAngewandte Chemie, 1995