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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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Supplementary files

Article information


Submitted
14 Mar 2012
Accepted
05 Jul 2012
First published
05 Jul 2012

Org. Biomol. Chem., 2012,10, 6629-6632
Article type
Communication

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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