A Non-Fluorinated Monobenzocyclooctyne for Rapid Copper-Free Click Reactions

作者:Varga Balazs R; Kallay Mihaly; Hegyi Krisztina; Beni Szabolcs; Kele Peter*
来源:Chemistry - A European Journal, 2012, 18(3): 822-828.
DOI:10.1002/chem.201102329

摘要

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).