Aliphatic polyamide dendrimers and dendrons with ethylenediamine (EDA), piperazine (PPZ) and methyl 2,2-bis(aminomethyl)propionate (COOMe) cores were synthesized by iterative divergent, convergent and double-stage convergent divergent methods. 2,2-Bis(azidomethyl)propionic acid was used as the starting AB<sub>2</sub> building block. A self-interruption of the synthesis was observed at a predictable generation number provided by the conformation rather than the multiplicity of the core. Molecular modelling demonstrated that this self-interruption is due to back-folding of the azide groups on the dendrimer periphery. These sterically hindered aliphatic polyamide dendrimers are both enzymatically and hydrolytically stable and revealed antimicrobial properties. Due to this combination of properties, together with their gram quantity synthesis, these nanoscale dendrimers offer numerous potential biomedical applications.

Self-interrupted synthesis of sterically hindered aliphatic polyamide dendrimers

254th National Meeting (2017)

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