‘Click’ Bioconjugation of a Well-Defined Synthetic Polymer and a Protein Transduction Domain

Jean-François Lutz; Hans G. Börner; Katja Weichenhan

doi:10.1071/CH07052

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‘Click’ Bioconjugation of a Well-Defined Synthetic Polymer and a Protein Transduction Domain

Jean-François Lutz ^A ^C , Hans G. Börner ^B and Katja Weichenhan ^A

+ Author Affiliations

- Author Affiliations

^A Research Group Nanotechnology for Life Science, Fraunhofer Institute for Applied Polymer Research, Geiselbergstrasse 69, Potsdam-Golm 14476, Germany.

^B Max Planck Institute of Colloids and Interfaces, Colloid Department, 14424 Potsdam-Golm, Germany.

^C Corresponding author. Email: lutz@iap.fhg.de

Australian Journal of Chemistry 60(6) 410-413 https://doi.org/10.1071/CH07052
Submitted: 17 February 2007 Accepted: 14 April 2007 Published: 18 June 2007

Abstract

The copper-catalyzed 1,3-dipolar ‘click’ cycloaddition of azides and alkynes was studied to link a model synthetic polymer to a sequence-defined protein transduction domain (PTD). The bromine chain-ends of a well-defined polystyrene (PS) sample synthesized by atom transfer radical polymerization (M_n 2200 g mol^–1, M_w/M_n 1.21) were first transformed into azide functions by substitution with sodium azide, and subsequently reacted with an alkyne-functionalized PTD (i.e., the oligopeptide sequence GGYGRKKRRQRRRG, also known as the TAT peptide). The click bioconjugation proceeded successfully at room temperature, thus affording the targeted PS-b-GGYGRKKRRQRRRG bioconjugate in high yields. However, a slight molar excess of polystyrene was required for optimal coupling.

Acknowledgments

J.F.L. thanks the Fraunhofer Society, Deutsche Forschungsgemeinschaft (DFG) (LU 1195/1-1), and the Federal Ministry of Education and Research (BMBF programs NanoforLife and NanoChem) for financial support. H.G.B. thanks DFG (Emmy Noether BO1762/2) for financial support. Moreover, the authors thank Dr Hartmut Rettig (MPI-KGF) and Katharina Otte (MPI-KGF) for their contribution to this project.

References

‘Click’ Bioconjugation of a Well-Defined Synthetic Polymer and a Protein Transduction Domain

Abstract

Acknowledgments

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