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Synthesis and application of the blue fluorescent amino acid L-4-cyanotryptophan to assess peptide–membrane interactions

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Abstract

Recently, L-4-cyanotryptophan has been shown to be an efficient blue fluorescence emitter, with the potential to enable novel applications in biological spectroscopy and microscopy. However, lack of facile synthetic routes to this unnatural amino acid limits its wide use. Herein, we describe an expedient approach to synthesize Fmoc protected L-4-cyanotryptophan with high optical purity (>99%). Additionally, we test the utility of this blue fluorophore in imaging cell-membrane-bound peptides and in determining peptide–membrane binding constants.

Graphical abstract: Synthesis and application of the blue fluorescent amino acid l-4-cyanotryptophan to assess peptide–membrane interactions

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Publication details

The article was received on 08 Feb 2019, accepted on 02 Apr 2019 and first published on 02 Apr 2019


Article type: Communication
DOI: 10.1039/C9CC01152H
Citation: Chem. Commun., 2019, Advance Article

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    Synthesis and application of the blue fluorescent amino acid L-4-cyanotryptophan to assess peptide–membrane interactions

    K. Zhang, I. A. Ahmed, H. T. Kratochvil, W. F. DeGrado, F. Gai and H. Jo, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC01152H

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