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  • Title: A tryptophan-containing open-chain framework for tuning a high selectivity for Ca2+ and 13C NMR observation of a Ca2+-indole interaction in aqueous solution.
    Author: Li Y, Yang CM.
    Journal: J Am Chem Soc; 2005 Mar 16; 127(10):3527-30. PubMed ID: 15755174.
    Abstract:
    Two molecular architectures featuring the cation-responsive tryptophan indole were designed and investigated for the development of a novel fluorescent chemosensor for Ca2+. We observed that the Trp-based open-framework chemosensor EW2 exhibits remarkable selectivity for Ca2+ over Mg2+, Ba2+, K+, Na+, and Li+ in water between pH 4.6 and 7.0 on the basis of Ca2+-induced high fluorescence enhancement of the Trp residue. A combined 13C NMR and CD spectroscopic study has demonstrated a dynamic reorientation of the indole ring due to the cation-indole interaction accompanying the Ca2+-induced dramatic fluorescence enhancement. The results suggest that the highly sensitive, metal-ion-dependent Trp indolyl C(3) chemical shifts may serve as a promising indicator for monitoring metal ion-indole noncovalent interaction in solution.
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