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Article Dans Une Revue Analytica Chimica Acta Année : 2015

Structural characterization of new defective molecules in poly(amidoamide)dendrimers by combining mass spectrometry and nuclear magnetic resonance

Résumé

A new side-reaction occurring during divergent synthesis of PAMAM dendrimers (generations G(0)-G(2)) was revealed by mass spectrometric detection of defective molecules with a net gain of a single carbon atom as compared to expected compounds. Combining MS/MS experiments performed on different electrosprayed precursor ions (protonated molecules and lithiated adducts) with NMR analyses allowed the origin of these by-products to be elucidated. Modification of one ethylenediamine end-group of perfect dendrimers into a cyclic imidazolidine moiety was induced by formaldehyde present at trace level in the methanol solvent used as the synthesis medium. Dendrimers studied here were purposely constructed from a triethanolamine core to make them more flexible, as compared to NH3- or ethylenediamine-core PAMAM, and hence improve their interaction with DNA. Occurrence of this side-reaction would be favored by the particular flexibility of the dendrimer branches.

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Chimie
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Dates et versions

hal-01128946 , version 1 (10-03-2015)

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Aura Tintaru, Rémi Ungaro, Xiaoxiuan Liu, Chao Chen, Laurent Giordano, et al.. Structural characterization of new defective molecules in poly(amidoamide)dendrimers by combining mass spectrometry and nuclear magnetic resonance. Analytica Chimica Acta, 2015, 853, pp.451-459. ⟨10.1016/j.aca.2014.10.048⟩. ⟨hal-01128946⟩
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