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Stepwise synthesis of oligonucleotide-peptide conjugates containing guanidinium and lipophilic groups in their 3'-termini

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Two different series of oligonucleotide-peptide conjugates have been efficiently synthesized by stepwise solid-phase synthesis. First, oligonucleotides and oligonucleotide phosphorothioates containing polar groups at the 3′-termini, such as amine and guanidinium groups were prepared. ODNs conjugates carrying several lysine residues were obtained directly from Fmoc deprotection whereas ODN conjugates with guanidinium groups were obtained by post-synthetic guanidinylation. The second family contains different urea moieties that were achieved by standard protocols. All products were fully characterized by reversed phase HPLC and MALDI-TOF mass spectrometry yielding satisfactory results. Oligonucleotide-phosphorothioate conjugates were evaluated as potential antisense oligonucleotides in the inhibition of the luciferase gene.

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GRIJALVO, Santiago, TERRAZAS MARTÍNEZ, Montserrat, AVIÑÓ ANDRÉS, Anna, ERITJA I CASADELLÀ, Ramon. Stepwise synthesis of oligonucleotide-peptide conjugates containing guanidinium and lipophilic groups in their 3'-termini. _Bioorganic & Medicinal Chemistry Letters_. 2010. Vol. 20, núm. 7, pàgs. 2144-2147. [consulta: 23 de gener de 2026]. ISSN: 0960-894X. [Disponible a: https://hdl.handle.net/2445/179826]

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