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Royal Society of Chemistry, Organic and Biomolecular Chemistry, 33(10), p. 6629, 2012

DOI: 10.1039/c2ob25556a

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Evaluation of bicinchoninic acid as a ligand for copper(i)-catalyzed azide–alkyne bioconjugations

This paper is available in a repository.
This paper is available in a repository.

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Abstract

Dieser Beitrag ist mit Zustimmung des Rechteinhabers aufgrund einer (DFG geförderten) Allianz- bzw. Nationallizenz frei zugänglich. ; This publication is with permission of the rights owner freely accessible due to an Alliance licence and a national licence (funded by the DFG, German Research Foundation) respectively. ; 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. ; EC/FP7/259043/EU/Computing Biomaterials/COMPBIOMAT ; DFG, EXC 294, BIOSS Zentrum für Biologische Signalstudien - von der Analyse zur Synthese ; DFG, GSC 4, Spemann Graduiertenschule für Biologie und Medizin (SGBM)