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A Non‐Fluorinated Monobenzocyclooctyne for Rapid Copper‐Free Click Reactions
Author(s) -
Varga Balázs R.,
Kállay Mihály,
Hegyi Krisztina,
Béni Szabolcs,
Kele Péter
Publication year - 2012
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.201102329
Subject(s) - bioorthogonal chemistry , click chemistry , glycan , reagent , fluorescence , chemistry , hela , combinatorial chemistry , biomolecule , labelling , copper , kinetics , biochemistry , cell , organic chemistry , glycoprotein , physics , quantum mechanics
We designed and synthesised carboxymethylmonobenzocyclooctyne (COMBO) through a four‐step reaction pathway. COMBO is a new, structurally simple, non‐fluorinated, and directly conjugable copper‐free click reagent, which shows excellent reaction kinetics, as also evidenced by theoretical calculations. Additionally, the carboxylic acid appendage allows further conjugation to biomolecules or fluorescent labels. The utility of COMBO in bioorthogonal labelling schemes was demonstrated when a COMBO‐containing fluorescent label was employed in glycan imaging of HeLa cells (metabolically modified to have azidosialic acid residues on their cell‐surface glycans).