A Trisbenzimidazole Phosphoramidite Building Block Enables High-Yielding Syntheses of RNA-Cleaving Oligonucleotide Conjugates
Abstract
:1. Introduction
2. Results
3. Discussion
4. Materials and Methods
4.1. General
4.2. Synthesis, Purification, Quantification and Analysis of Conjugates
4.2.1. Manual Phosphoramidite Coupling
4.2.2. Isolation and Purification
4.2.3. Quantification
4.2.4. Mass spectrometry
4.2.5. Cleavage Studies
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Conjugate | t1/2 | n − 2 | n − 1 | n | n + 1 | n + 2 | n + 3 |
---|---|---|---|---|---|---|---|
31,3 | 14 ± 0.9 h | 1.4% | 2.5% | 89.0% | 7.1% | ||
41,3 | 3.5 ± 0.4 h | 1.6% | 5.8% | 83.9% | 8.6% | ||
131 | 13.3 ± 0.8 h | 1.5% | 65.2% | 30.2% | 3.1% | ||
141 | 6.4 ± 0.2 h | 1.2% | 75.3% | 22.1% | 1.4% | ||
151 | 6.5 ± 0.5 h | 1.5% | 88.3% | 10.1% | |||
161 | 5.6 ± 0.1 h | 1.2% | 74.9% | 22.1% | 1.7% | ||
52,3 | 15.0 ± 1.7 h | 29.0% | 22.7% | 35.8% | 5.1% | 3.6% | |
62,3 | 10.0 ± 0.3 h | 6.4% | 35.0% | 45.9% | 6.9% | 4.5% | 1.3% |
172 | 18.3 ± 1.2 h | 5.2% | 4.1% | 52.1% | 22.5% | 9.6% | 2.3% |
182 | 14.2 ± 0.7 h | 2.4% | 67.4% | 21.8% | 6.1% | 2.2% | |
192 | 13.0 ± 1.5 h | 10.7% | 71.3% | 9.8% | 6.4% | 1.8% | |
202 | 9.8 ± 1.0 h | 3.2% | 72.4% | 17.2% | 3.4% | 1.1% |
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Zellmann, F.; Göbel, M.W. A Trisbenzimidazole Phosphoramidite Building Block Enables High-Yielding Syntheses of RNA-Cleaving Oligonucleotide Conjugates. Molecules 2020, 25, 1842. https://doi.org/10.3390/molecules25081842
Zellmann F, Göbel MW. A Trisbenzimidazole Phosphoramidite Building Block Enables High-Yielding Syntheses of RNA-Cleaving Oligonucleotide Conjugates. Molecules. 2020; 25(8):1842. https://doi.org/10.3390/molecules25081842
Chicago/Turabian StyleZellmann, Felix, and Michael W. Göbel. 2020. "A Trisbenzimidazole Phosphoramidite Building Block Enables High-Yielding Syntheses of RNA-Cleaving Oligonucleotide Conjugates" Molecules 25, no. 8: 1842. https://doi.org/10.3390/molecules25081842