Next Article in Journal
GC-MS and HS-SPME-GC×GC-TOFMS Determination of the Volatile Composition of Essential Oils and Hydrosols (By-Products) from Four Eucalyptus Species Cultivated in Tuscany
Next Article in Special Issue
Aptamer Efficacies for In Vitro and In Vivo Modulation of αC-Conotoxin PrXA Pharmacology
Previous Article in Journal
Mechanical and Tribological Properties of Polytetrafluoroethylene Composites with Carbon Fiber and Layered Silicate Fillers
Previous Article in Special Issue
Selection, Characterization, and Application of ssDNA Aptamer against Furaneol
Article Menu
Issue 2 (January-2) cover image

Export Article

Open AccessFeature PaperArticle
Molecules 2019, 24(2), 225;

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
Author to whom correspondence should be addressed.
Academic Editors: Shigeki Sasaki and Marcel Hollenstein
Received: 21 December 2018 / Revised: 5 January 2019 / Accepted: 7 January 2019 / Published: 9 January 2019
Full-Text   |   PDF [1250 KB, uploaded 9 January 2019]   |  


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

Figure 1

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).

Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top