A non-fluorinated monobenzocyclooctyne for rapid copper-free click reactions

Balázs R. Varga, Mihály Kállay, Krisztina Hegyi, Szabolcs Béni, Péter Kele

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)822-828
Number of pages7
JournalChemistry - A European Journal
Volume18
Issue number3
DOIs
Publication statusPublished - Jan 16 2012

Keywords

  • bioorthogonal labelling
  • click chemistry
  • cyclooctynes
  • fluorescent probes
  • strained molecules

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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