This research was supported by grants from the German Research Foundation (SFB670, SFB704) to G.H. M.G., G.H., and J.L. are funded by the excellence cluster Immunosensation. We thank Dr. I. Roehl and S. Seiffert (Axolabs GmbH, Analytics) for measurement of the LC–MS spectra and helpful discussions. pppRNA=5′-triphosphate RNA.
Efficient Solid-Phase Synthesis of pppRNA by Using Product-Specific Labeling†
Article first published online: 25 MAR 2014
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 53, Issue 18, pages 4694–4698, April 25, 2014
How to Cite
Goldeck, M., Tuschl, T., Hartmann, G. and Ludwig, J. (2014), Efficient Solid-Phase Synthesis of pppRNA by Using Product-Specific Labeling. Angew. Chem. Int. Ed., 53: 4694–4698. doi: 10.1002/anie.201400672
- Issue published online: 25 APR 2014
- Article first published online: 25 MAR 2014
- Manuscript Received: 21 JAN 2014
- German Research Foundation
- medicinal chemistry;
A novel solid-phase synthesis and purification strategy for 5′-triphosphate oligonucleotides by using lipophilic tagging of the triphosphate moiety is reported. This is based on triphosphate synthesis with 5′-O-cyclotriphosphate intermediates, whereby a lipophilic tag, such as decylamine, is introduced during the ring-opening reaction to give a linear gamma-phosphate-tagged species. This method enables the highly efficient synthesis of 5′-triphosphorylated RNA derivatives and their gamma-phosphate-substituted analogues and will especially facilitate the advancement of therapeutic approaches that make use of 5′-triphosphate oligonucleotides as potent activators of the cytosolic immune sensor RIG-I.