Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Facile Synthesis of the Uryl Pendant Binaphthol Aldehyde and Its Selective Fluorescent Recognition of Tryptophan

  • Tang, Lijun (College of Chemistry and Chemical Engineering, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University) ;
  • Wei, Gongfan (College of Chemistry and Chemical Engineering, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University) ;
  • Nandhakumar, Raju (Department of Chemistry, Karunya University) ;
  • Guo, Zhilong (College of Chemistry and Chemical Engineering, Liaoning Key Laboratory for the Synthesis and Application of Functional Compounds, Bohai University)
  • Received : 2011.01.03
  • Accepted : 2011.07.27
  • Published : 2011.09.20
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Abstract

An easy and convenient synthetic route to (S)-2-hydroxy-2'-(3-phenyluryl-benzyl)-1,1'-binaphthyl-3-carboxaldehyde (1), capable of recognizing tryptophan by fluorescence has been developed. The binol carboxaldehyde 1 exhibited a high selectivity to L-tryptophan over other examined L-${\alpha}$-amino acids such as alanine, phenylalanine, glutamine, arginine, lysine, serine, threonine, aspartat, valine, histidine and cysteine, with a fluorescence "turn-on" signal. In addition, 1 displayed chiral discrimination with good enantioselectivity toward L-tryptophan over D-tryptophan through different fluorescence enhancement factors.

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References

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