Journal of Organic Chemistry 2010-10-01

Isopropylamino and isobutylamino groups as recognition sites for carbohydrates: acyclic receptors with enhanced binding affinity toward β-galactosides.

Monika Mazik, Claudia Sonnenberg

Index: J. Org. Chem. 75(19) , 6416-23, (2010)

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Abstract

Binding motifs observed in the crystal structures of protein-carbohydrate complexes, in particular the participation of the isopropyl/isobutyl side chain of valine/leucine in the formation of van der Waals contacts, have inspired the design of new artificial carbohydrate receptors. The new compounds, containing a trisubstituted triethylbenzene core, were expected to recognize sugar molecules through a combination of NH···O and OH···N hydrogen bonds, CH···π interactions, and numerous van der Waals contacts. (1)H NMR spectroscopic titrations in competitive and noncompetitive media, as well as binding studies in two-phase systems, such as dissolution of solid carbohydrates in apolar media and phase transfer of sugars from aqueous into organic solvents, revealed effective recognition of neutral carbohydrates and β- vs α-anomer binding preferences in the recognition of glycosides as well as significantly increased binding affinity of the receptors toward β-galactoside in comparison with the previously described receptors.