1,1′-Binaphthyl-based imidazolium chemosensors for highly selective recognition of tryptophan in aqueous solutions?

Organic & Biomolecular Chemistry Pub Date: 2009-11-17 DOI: 10.1039/B908540H

Abstract

A type of 1,1′-binaphthyl-based imidazolium chemosensor module has been synthesized for the highly selective recognition of tryptophan (Trp) among the eleven α-amino acids investigated in aqueous solutions via synergistic effects of multiple hydrogen bonding and electrostatic interactions. These results have demonstrated that the C-2 hydrogen atom of the imidazolium ring plays a key role as a hydrogen bond donor. The UV/vis, fluorescence and mass spectral studies have indicated that a 1?:?1 complex is formed between the host and tryptophan. The binding affinity and selectivity of the cleft-like receptor (R)-1 with L-Trp are superior to those of (R)-2–5. In spite of an inferior selectivity towards various aromatic amino acids, the macrocyclic (R)-3 displays a remarkable enantiodiscrimination for the two enantiomers of tryptophan with a KD/KL value as high as 6.2.

Graphical abstract: 1,1′-Binaphthyl-based imidazolium chemosensors for highly selective recognition of tryptophan in aqueous solutions
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