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http://dx.doi.org/10.5012/bkcs.2011.32.9.3367

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)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.9, 2011 , pp. 3367-3371 More about this Journal
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.
Keywords
Tryptophan; Recognition; Enantioselectivity; Fluorescence; Binaphthol;
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