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Int. J. Mol. Sci. 2015, 16(6), 12631-12647; doi:10.3390/ijms160612631

Efficient Synthesis of Peptide and Protein Functionalized Pyrrole-Imidazole Polyamides Using Native Chemical Ligation

Laboratory of Chemical Biology and Institute for Complex Molecular Systems, Eindhoven University of Technology, Den Dolech 2, 5600 MB Eindhoven, The Netherlands
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Academic Editor: Eric C. Long
Received: 24 March 2015 / Revised: 25 May 2015 / Accepted: 28 May 2015 / Published: 4 June 2015
(This article belongs to the Special Issue Low Molecular Weight DNA and RNA Binding Agents)
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Abstract

The advancement of DNA-based bionanotechnology requires efficient strategies to functionalize DNA nanostructures in a specific manner with other biomolecules, most importantly peptides and proteins. Common DNA-functionalization methods rely on laborious and covalent conjugation between DNA and proteins or peptides. Pyrrole-imidazole (Py–Im) polyamides, based on natural minor groove DNA-binding small molecules, can bind to DNA in a sequence specific fashion. In this study, we explore the use of Py–Im polyamides for addressing proteins and peptides to DNA in a sequence specific and non-covalent manner. A generic synthetic approach based on native chemical ligation was established that allows efficient conjugation of both peptides and recombinant proteins to Py–Im polyamides. The effect of Py–Im polyamide conjugation on DNA binding was investigated by Surface Plasmon Resonance (SPR). Although the synthesis of different protein-Py–Im-polyamide conjugates was successful, attenuation of DNA affinity was observed, in particular for the protein-Py–Im-polyamide conjugates. The practical use of protein-Py–Im-polyamide conjugates for addressing DNA structures in an orthogonal but non-covalent manner, therefore, remains to be established. View Full-Text
Keywords: pyrrole-imidazole polyamides; DNA-functionalization; native chemical ligation; DNA-nanotechnology; surface plasmon resonance pyrrole-imidazole polyamides; DNA-functionalization; native chemical ligation; DNA-nanotechnology; surface plasmon resonance
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Janssen, B.M.G.; van Ommeren, S.P.F.I.; Merkx, M. Efficient Synthesis of Peptide and Protein Functionalized Pyrrole-Imidazole Polyamides Using Native Chemical Ligation. Int. J. Mol. Sci. 2015, 16, 12631-12647.

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