title: Evaluation of bicinchoninic acid as a ligand for copper(I)-catalyzed azide-alkyne bioconjugations.
abstract: The Cu(I)-catalyzed cycloaddition of terminal azides and alkynes (click chemistry) represents a highly specific reaction for the functionalization of biomolecules with chemical moieties such as dyes or polymer matrices. In this study we evaluate the use of bicinchoninic acid (BCA) as a ligand for Cu(I) under physiological reaction conditions. We demonstrate that the BCA-Cu(I)-complex represents an efficient catalyst for the conjugation of fluorophores or biotin to alkyne- or azide-functionalized proteins resulting in increased or at least equal reaction yields compared to commonly used catalysts like Cu(I) in complex with TBTA (tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine) or BPAA (bathophenanthroline disulfonic acid). The stabilization of Cu(I) with BCA represents a new strategy for achieving highly efficient bioconjugation reactions under physiological conditions in many application fields.
authors: Faculty of Biology, University of Freiburg, Germany.
authors: Erik H
authors: EH
authors: Christen
authors: Raphael J
authors: RJ
authors: Gübeli
authors: Beate
authors: B
authors: Kaufmann
authors: Lars
authors: L
authors: Merkel
authors: Ronald
authors: R
authors: Schoenmakers
authors: Nediljko
authors: N
authors: Budisa
authors: Martin
authors: M
authors: Fussenegger
authors: Wilfried
authors: W
authors: Weber
authors: Birgit
authors: B
authors: Wiltschi
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry / Q000379:methods; D004396:Coloring Agents / Q000737:chemistry; D056831:Coordination Complexes / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D061565:Cycloaddition Reaction / Q000379:methods; D008024:Ligands; D008049:Lipase / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*; D046968:Thermoanaerobacter / Q000201:enzymology
chemical_list: D000480:Alkynes; D001386:Azides; D004396:Coloring Agents; D056831:Coordination Complexes; D008024:Ligands; D011804:Quinolines; D003300:Copper; C047117:bicinchoninic acid; D008049:Lipase