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Issue 33, 2012
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Evaluation of bicinchoninic acid as a ligand for copper(I)-catalyzed azide–alkyne bioconjugations

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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.

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

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Publication details

The article was received on 14 Mar 2012, accepted on 05 Jul 2012 and first published on 05 Jul 2012


Article type: Communication
DOI: 10.1039/C2OB25556A
Citation: Org. Biomol. Chem., 2012,10, 6629-6632

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

    E. H. Christen, R. J. Gübeli, B. Kaufmann, L. Merkel, R. Schoenmakers, N. Budisa, M. Fussenegger, W. Weber and B. Wiltschi, Org. Biomol. Chem., 2012, 10, 6629
    DOI: 10.1039/C2OB25556A

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