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© Research
Publication : Bioorganic and Medicinal Chemistry Letters

Towards the enzymatic synthesis of phosphorothioate containing LNA oligonucleotides

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Bioorganic and Medicinal Chemistry Letters - 07 Jul 2021

Marie Flamme, Steven Hanlon, Hans Iding, Kurt Puentener, Filippo Sladojevich, Marcel Hollenstein*

Link to DOI – 10.1016/j.bmcl.2021.128242

Bioorg. Med. Chem. Lett. 48 (2021) 128242

Therapeutic oligonucleotides require the addition of multiple chemical modifications to the nucleosidic scaffold in order to improve their drug delivery efficiency, cell penetration capacity, biological stability, and pharmacokinetic properties. This chemical modification pattern is often accompanied by a synthetic burden and by limitations in sequence length. Here, we have synthesized a nucleoside triphosphate analog bearing two simultaneous modifications at the level of the sugar (LNA) and the backbone (thiophosphate) and have tested its compatibility with enzymatic DNA synthesis which could abrogate some of these synthetic limitations. While this novel analog is not as well tolerated by polymerases compared to the corresponding α-thio-dTTP or LNA-TTP, α -thio-LNA-TTP can readily be used for enzymatic synthesis on universal templates for the introduction of phosphorothioated LNA nucleotides.

https://www.sciencedirect.com/science/article/pii/S0960894X21004698?via%3Dihub