| 20066268 |
Yang L, Qin S, Su X, Yang F, You J, Hu C, Xie R, Lan J: 1,1'-Binaphthyl-based imidazolium chemosensors for highly selective recognition of tryptophan in aqueous solutions. Org Biomol Chem. 2010 Jan 21;8(2):339-48. Epub 2009 Nov 17.
A type of 1,1'-binaphthyl-based imidazolium chemosensor module has been synthesized for the highly selective recognition of tryptophan (Trp) among the eleven alpha-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)- with l-Trp are superior to those of (R)-. In spite of an inferior selectivity towards various aromatic amino acids, the macrocyclic (R)- displays a remarkable enantiodiscrimination for the two enantiomers of tryptophan with a K (D)/K (L) value as high as 6.2. |
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