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A Double‐Clicking Bis‐Azide Fluorogenic Dye for Bioorthogonal Self‐Labeling Peptide Tags
Author(s) -
Demeter Orsolya,
Fodor Eszter A.,
Kállay Mihály,
Mező Gábor,
Németh Krisztina,
Szabó Pál T.,
Kele Péter
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504939
Subject(s) - bioorthogonal chemistry , azide , peptide , chemistry , click chemistry , combinatorial chemistry , cycloaddition , fluorescence , alkyne , biochemistry , organic chemistry , physics , quantum mechanics , catalysis
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.