title: A non-fluorinated monobenzocyclooctyne for rapid copper-free click reactions.
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).
authors.affiliation: Institute of Chemistry, Eötvös Loránd University, H-1117 Pázmány Péter stny 1a, Budapest, Hungary.
authors.forename: Balázs R
authors.initials: BR
authors.lastname: Varga
authors.forename: Mihály
authors.initials: M
authors.lastname: Kállay
authors.forename: Krisztina
authors.initials: K
authors.lastname: Hegyi
authors.forename: Szabolcs
authors.initials: S
authors.lastname: Béni
authors.forename: Péter
authors.initials: P
authors.lastname: Kele
mesh_terms: D000818:Animals; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D006224:Cricetinae; D034242:Cyclooctanes / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D011134:Polysaccharides / Q000032:analysis
chemical_list: D034242:Cyclooctanes; D005456:Fluorescent Dyes; D011134:Polysaccharides; C571502:carboxymethylmonobenzocyclooctyne; D003300:Copper