Dendrons are interesting macromolecules, because they allow the orthogonal derivatization of one focal and several terminal groups in highly branched architectures. Biocompatible hyperbranched polglycerol dendron analogues containing exactly one focal amino group and multiple terminal hydroxyl groups were synthesized with control over molecular weight (Mn=1000-5000 g mol-1, Mw/Mn = 1.5-1.8) in a facile three-step synthesis protocol. First, the novel trifunctional initiator N,N-dibenzyl tris(hydroxymethyl) aminomethane (Bn2TRIS) was synthesized. After the addition of glycidol to build up the hyperbranched structure with several terminal hydroxyl groups via slow monomer-addition (SMA), the benzyl protective groups of the initiator were removed by hydrogenation using Pd(OH)2/C as catalyst in the third step to release the focal amino group. The polymers were characterized in detail using 1H and 13C NMR spectroscopy, size exclusion chromatography as well as MALDI-ToF mass spectrometry. The amino function renders the biocompatible polymers interesting for further derivatizations, e.g., bioconjugation reactions.

Hyperbranched polyglycerol dendron analogues with a focal amino functionality

243rd National Meeting (2012)

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