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Synthesis and Biophysical Properties of Phosphorodiamidate Piperidino Oligomers. 2023
Atanu Ghosh, and
Masaaki Akabane-Nakata, and
Jayanta Kundu, and
Joel M Harp, and
Mimouna Madaoui, and
Martin Egli, and
Muthiah Manoharan, and
Surajit Sinha
School of Applied and Interdisciplinary Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
We report the synthesis of piperidino nucleoside phosphoramidates functionalized with uracil, cytosine, guanine, and adenine and their incorporation into oligomers. High-performance liquid chromatography analyses demonstrated that a phosphorodiamidate piperidino oligomer (PPO) is more lipophilic than a phosphorodiamidate morpholino oligomer (PMO) of the same tetrameric sequence. A PMO containing piperidino residues formed duplexes with both DNA and RNA, and the PPO had higher stability at endosomolytic pH and higher hydrophobicity than the PMO.
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