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Journal Article

Peptide-functionalized polyphenylene dendrimers

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons48026

Herrmann,  A.
MPI for Polymer Research, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons48429

Mihov,  G.
MPI for Polymer Research, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons48905

Vandermeulen,  G. W. M.
MPI for Polymer Research, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons48195

Klok,  Harm-Anton
MPI for Polymer Research, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons48459

Müllen,  Klaus
MPI for Polymer Research, Max Planck Society;

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Citation

Herrmann, A., Mihov, G., Vandermeulen, G. W. M., Klok, H.-A., & Müllen, K. (2003). Peptide-functionalized polyphenylene dendrimers. Tetrahedron, 59(22), 3925-3935.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-61F2-F
Abstract
This contribution describes the synthesis of polyphenylene dendrimers that are functionalized with up to 16 lysine residues or substituted with short peptide sequences composed of 5 lysine or glutamic acid repeats and a C- or N-terminal cysteine residue. Polyphenylene dendrimers were prepared via a sequence of Diels-Alder cycloaddition and deprotection reactions from cyclopentadienone building blocks. Single amino acids could be introduced on the periphery of the dendrimers by using amino acid substituted cyclopentadienones in the last Diels-Alder addition reaction. Alternatively, peptide sequences were attached via a chemoselective reaction, which involved the addition of the sulfhydryl group of a cysteine residue of an oligopeptide to a maleimide moiety present on the surface of the dendrimer. These amino acid and peptide functionalized dendrimers may be of interest as model compounds to study DNA complexation and condensation or as building blocks for the preparation of novel supramolecular architectures via layer-by-layer self-assembly. (C) 2003 Elsevier Science Ltd. All rights reserved.