Molecules, Vol. 24, Pages 225: S-Acyl-2-Thioethyl: A Convenient Base-Labile Protecting Group for the Synthesis of siRNAs Containing 5 ′-Vinylphosphonate

Molecules, Vol. 24, Pages 225: S-Acyl-2-Thioethyl: A Convenient Base-Labile Protecting Group for the Synthesis of siRNAs Containing 5′-Vinylphosphonate Molecules doi: 10.3390/molecules24020225 Authors: Mehran Nikan Wenyu Li Garth A. Kinberger Punit P. Seth Eric E. Swayze Thazha P. Prakash 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.
Source: Molecules - Category: Chemistry Authors: Tags: Article Source Type: research
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