Carboxyalkyl peptoid PNAs: synthesis and hybridization properties |
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Authors: | Chiara De Cola Alex Manicardi Roberto Corradini Irene Izzo Francesco De Riccardis |
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Institution: | 1. Dipartimento di Chimica e Biologia, Università di Salerno, Via Ponte don Melillo, Fisciano (SA) 84084, Italy;2. Dipartimento di Chimica Organica e Industriale, Università di Parma, Parco Area delle Scienze 17/A, Parma 43124, Italy |
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Abstract: | Nγ-Carboxyalkyl modified peptide nucleic acids (PNAs), containing the four canonical nucleobases, were prepared via solid-phase oligomerization. The inserted peptoid monomers 1 and 2 were constructed through simple synthetic procedures, utilizing appropriate glycidol and iodoalkyl electrophiles. Thermal denaturation studies, performed with complementary antiparallel DNA strands, demonstrated that the length of the Nγ-side chain strongly influences the modified PNAs hybridization properties. Moreover, multiple negative charges on the oligoamide backbone, when present on γ-nitrogen C6 side chains proved to be beneficial for the oligomers’ water solubility and DNA hybridization specificity. |
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