The synthesis of solid supports carrying base labile linkers to generate 3′-phosphate oligonucleotides

[Display omitted] •Oligonucleotide carrying 3′-phosphates are important molecules in biomedicine.•Solid supports functionalized with base labile linkers allow the rapid preparation of these compounds.•The 4-((2-hydroxyethyl)sulfonyl)benzamide linker provides excellent yields in the preparation of 3′...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2024-09, Vol.109, p.129819, Article 129819
Hauptverfasser: Masuku, Kwazi, Menéndez-Méndez, Luis Miguel, Noki, Sikabwe, de la Torre, Beatriz G., Albericio, Fernando, Fernández, Susana, Ferrero, Miguel, Aviñó, Anna, Eritja, Ramon, Fàbrega, Carme
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Sprache:eng
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Zusammenfassung:[Display omitted] •Oligonucleotide carrying 3′-phosphates are important molecules in biomedicine.•Solid supports functionalized with base labile linkers allow the rapid preparation of these compounds.•The 4-((2-hydroxyethyl)sulfonyl)benzamide linker provides excellent yields in the preparation of 3′-phosphorylated oligonucleotides.•Mild deprotection conditions allows the preparation of partially protected DNA fragments. Oligonucleotides carrying 3′-terminal phosphates and conjugates are important tools in molecular biology and diagnostic purposes. We described the preparation of solid supports carrying the base labile linker 4-((2-hydroxyethyl)sulfonyl)benzamide for the solid-phase synthesis of 3′-phosphorylated oligonucleotides. These supports are fully compatible with the phosphoramidite chemistry yielding the desired 3′-phosphate oligonucleotides in excellent yields. The use of mild deprotection conditions allows the generation of partially protected DNA fragments.
ISSN:0960-894X
1464-3405
1464-3405
DOI:10.1016/j.bmcl.2024.129819