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Issue 16, 2014
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Versatile C3-symmetric scaffolds and their use for covalent stabilization of the foldon trimer

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Abstract

C 3-Symmetric trimesic acid scaffolds, functionalized with bromoacetyl, aminooxyacetyl and azidoacetyl moieties, respectively, were synthesized and compared regarding their utility for the trivalent presentation of peptides using three different chemoselective ligation reactions, i.e. thioether and oxime formation, as well as the “click” reaction. The latter ligation method was then used to covalently stabilize the trimer of foldon, a 27 amino acid trimerization domain of bacteriophage T4 fibritin, by linking the three foldon monomers to the triazido-functionalized trimesic acid scaffold. This reaction dramatically enhanced the thermal stability of the trimer, while maintaining the correct fold, as demonstrated by CD spectroscopy and X-ray crystal structure analysis, respectively, of the foldon–scaffold conjugates.

Graphical abstract: Versatile C3-symmetric scaffolds and their use for covalent stabilization of the foldon trimer

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Publication details

The article was received on 12 Nov 2013, accepted on 18 Feb 2014 and first published on 18 Feb 2014


Article type: Paper
DOI: 10.1039/C3OB42251H
Citation: Org. Biomol. Chem., 2014,12, 2606-2614
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    Versatile C3-symmetric scaffolds and their use for covalent stabilization of the foldon trimer

    A. Berthelmann, J. Lach, M. A. Gräwert, M. Groll and J. Eichler, Org. Biomol. Chem., 2014, 12, 2606
    DOI: 10.1039/C3OB42251H

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