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Issue 35, 2019
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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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Supplementary files

Article information


Submitted
08 Feb 2019
Accepted
02 Apr 2019
First published
02 Apr 2019

Chem. Commun., 2019,55, 5095-5098
Article type
Communication

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, 55, 5095
DOI: 10.1039/C9CC01152H

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