Towards click bioconjugations on cube-octameric silsesquioxane scaffolds

Sebastian Fabritz; Dirk Heyl; Viktor Bagutski; Martin Empting; Eckhard Rikowski; Holm Frauendorf; Ildiko Balog; Wolf-Dieter Fessner; Jörg. J. Schneider; Olga Avrutina; Harald Kolmar

doi:10.1039/B923393H

Towards click bioconjugations on cube-octameric silsesquioxane scaffolds†

Sebastian Fabritz,^a Dirk Heyl,^a Viktor Bagutski,^b Martin Empting,^a Eckhard Rikowski,^c Holm Frauendorf,^d Ildiko Balog,^c Wolf-Dieter Fessner,^a Jörg. J. Schneider,^c Olga Avrutina^a and Harald Kolmar*^a

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* Corresponding authors

^a Clemens Schöpf Institute of Organic Chemistry and Biochemistry, Technische Universität Darmstadt, Petersenstr. 22, Darmstadt, Germany

^b School of Chemistry, Bristol University, Cantock's Close, Bristol, UK

^c Eduard Zintl Institute of Inorganic Chemistry, Technische Universität Darmstadt, Petersenstr. 22, Darmstadt, Germany

^d Institute of Organic and Biomolecular Chemistry, Georg-August Universität Göttingen, Tamannstraße 2, Göttingen, Germany

Abstract

Cube-octameric silsesquioxane (POSS) based conjugation scaffolds for copper catalysed azide-alkyne [3+2] cycloaddition are reported. The synthetic route to octaazido and octaalkyno functionalised POSS templates without cage rearrangements is described. A set of click couplings is conducted including the first effective conjugation with a fully unprotected functional peptide towards a POSS assembled peptide octamer.

Organic & Biomolecular Chemistry

Towards click bioconjugations on cube-octameric silsesquioxane scaffolds†

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