title: Rapid formation of a stable boron-nitrogen heterocycle in dilute, neutral aqueous solution for bioorthogonal coupling reactions.
abstract: Combining 2-formylphenylboronic acid with 4-hydrazinylbenzoic acid in neutral aqueous solution at low, equimolar concentrations of the reagents results in a single, stable product, a 1,2-dihydro-1-hydroxy-2,3,1-benzodiazaborine, in a matter of minutes with no side products. Application of this reaction to protein conjugation demonstrates that the reaction is orthogonal to protein functional groups, and the resulting conjugate withstands SDS-PAGE analysis. This reaction should be particularly useful for couplings that must be performed with low concentrations of reagents under physiologically compatible conditions.
authors.affiliation: Department of Medical Biochemistry, School of Medicine, Istanbul Kemerburgaz University, Bagcilar, Istanbul 34217, Turkey. ozlem.dilek@kemerburgaz.edu.
authors.forename: Ozlem
authors.initials: O
authors.lastname: Dilek
authors.affiliation: Department of Chemistry, Binghamton University, State University of New York, Binghamton, NY 13902, USA. sbane@binghamton.edu.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Lei
authors.affiliation: Department of Chemistry, Binghamton University, State University of New York, Binghamton, NY 13902, USA. sbane@binghamton.edu.
authors.forename: Kamalika
authors.initials: K
authors.lastname: Mukherjee
authors.affiliation: Department of Chemistry, Binghamton University, State University of New York, Binghamton, NY 13902, USA. sbane@binghamton.edu.
authors.forename: Susan
authors.initials: S
authors.lastname: Bane
mesh_terms: D000818:Animals; D001547:Benzaldehydes / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000737:chemistry; D002417:Cattle; D003500:Cyclization; D004591:Electrophoresis, Polyacrylamide Gel; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D006834:Hydrazines / Q000737:chemistry; D006835:Hydrazones / Q000138:chemical synthesis; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D012710:Serum Albumin, Bovine / Q000737:chemistry
chemical_list: C532809:2-formylphenylboronic acid; D001547:Benzaldehydes; D001565:Benzoates; D001896:Boron Compounds; D001897:Boronic Acids; D006574:Heterocyclic Compounds, 2-Ring; D006834:Hydrazines; D006835:Hydrazones; D012710:Serum Albumin, Bovine