Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 3, Pages 822-828Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201102329
Keywords
bioorthogonal labelling; click chemistry; cyclooctynes; fluorescent probes; strained molecules
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Funding
- Hungarian Academy of Sciences
- European Research Council (ERC) under the European Community [FP7/2007-2013]
- ERC [200639]
- Hungarian Scientific Research Fund (OTKA) [NF72194]
- European Research Council (ERC) [200639] Funding Source: European Research Council (ERC)
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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).
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