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Molecules 2019, 24(2), 225; https://doi.org/10.3390/molecules24020225

S-Acyl-2-Thioethyl: A Convenient Base-Labile Protecting Group for the Synthesis of siRNAs Containing 5′-Vinylphosphonate

Ionis Pharmaceuticals Inc., 2855 Gazelle Ct, Carlsbad, CA 92008, USA
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Academic Editors: Shigeki Sasaki and Marcel Hollenstein
Received: 21 December 2018 / Revised: 5 January 2019 / Accepted: 7 January 2019 / Published: 9 January 2019
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Abstract

We recently reported that (E)-5′-vinylphosphonate (5′-VP) is a metabolically-stable phosphate mimic for siRNA and demonstrated that 5′-VP improves the potency of the fully modified siRNAs in vivo. Here, we report an alternative synthesis of 5′-VP modified guide strand using S-pivaloyl-2-thioethyl (tBu-SATE) protecting group. The tBu-SATE group is readily removed during the final cleavage of the oligonucleotide from the solid support and providing a more convenient route for the synthesis of siRNA guide strand carrying a 5′-vinylphosphonate. View Full-Text
Keywords: SATE; siRNA; vinylphosphonate SATE; siRNA; vinylphosphonate
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Nikan, M.; Li, W.; Kinberger, G.A.; Seth, P.P.; Swayze, E.E.; Prakash, T.P. S-Acyl-2-Thioethyl: A Convenient Base-Labile Protecting Group for the Synthesis of siRNAs Containing 5′-Vinylphosphonate. Molecules 2019, 24, 225.

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