A Double‐Clicking Bis‐Azide Fluorogenic Dye for Bioorthogonal Self‐Labeling Peptide Tags |
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| Authors: | Orsolya Demeter Eszter A Fodor Prof?Dr Mihály Kállay Prof?Dr Gábor Mez? Dr Krisztina Németh Dr Pál T Szabó Dr Péter Kele |
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| Institution: | 1. Chemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Budapest, Hungary;2. MTA-BME “Lendület” Quantum Chemistry Research Group, Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, Budapest, Hungary;3. MTA-ELTE Research Group of Peptide Chemistry, Hungarian Academy of Sciences, Budapest, Hungary;4. MS Metabolomics Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Budapest, Hungary). |
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| Abstract: | Herein, we give the very first example for the development of a fluorogenic molecular probe that combines the two‐point binding specificity of biarsenical‐based dyes with the robustness of bioorthogonal click‐chemistry. This proof‐of‐principle study reports on the synthesis and fluorogenic characterization of a new, double‐quenched, bis‐azide fluorogenic probe suitable for bioorthogonal two‐point tagging of small peptide tags by double strain‐promoted azide–alkyne cycloaddition. The presented probe exhibits remarkable increase in fluorescence intensity when reacted with bis‐cyclooctynylated peptide sequences, which could also serve as possible self‐labeling small peptide tag motifs. |
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| Keywords: | cycloaddition click chemistry dyes/pigments fluorescent probes peptides |
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