2,6-Bis(1,4,7,10-tetraazacyclododecan-1-ylmethyl)pyridine and Its Benzene Analog as Nonmetallic Cleaving Agents of RNA Phosphodiester Linkages
Abstract
:1. Introduction
2. Results
2.1. Synthesis of Cleaving Agents 11a and 11b
2.2. Determination of the pKa Values of the Cleaving Agents
2.3. Kinetic Measurements
Rate Constant | 11a | 11b | ||
---|---|---|---|---|
Cleavage | Isomerization | Cleavage | Isomerization | |
k5/10−3 L·mol−1·s−1 | 26.1 ± 0.2 | 6.2 ± 0.2 | N/A a | N/A a |
k4/10−3 L·mol−1·s−1 | 7.37 ± 0.06 | 4.7 ± 0.1 | 17.5 ± 0.4 | 15 ± 3 |
k3/10−3 L·mol−1·s−1 | N/A b | 0.5 ± 0.2 | 11.1 ± 0.8 | 4 ± 6 |
3. Discussion
3.1. Base-Selectivity of 11a
3.2. Mechanism of the Catalysis by 11a and 11b
4. Experimental Section
4.1. General Methods
4.2. 2,6-Bis(1,4,7,10-tetraazacyclododecan-1-ylmethyl)pyridine (11a)
4.3. 1,3-Bis(1,4,7,10-tetraazacyclododecan-1-ylmethyl)benzene (11b)
4.4. Determination of the pKa Values
4.5. Kinetic Measurements
5. Conclusions
Supplementary Materials
Author Contributions
Conflicts of Interest
References
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Lain, L.; Lahdenpohja, S.; Lönnberg, H.; Lönnberg, T. 2,6-Bis(1,4,7,10-tetraazacyclododecan-1-ylmethyl)pyridine and Its Benzene Analog as Nonmetallic Cleaving Agents of RNA Phosphodiester Linkages. Int. J. Mol. Sci. 2015, 16, 17798-17811. https://doi.org/10.3390/ijms160817798
Lain L, Lahdenpohja S, Lönnberg H, Lönnberg T. 2,6-Bis(1,4,7,10-tetraazacyclododecan-1-ylmethyl)pyridine and Its Benzene Analog as Nonmetallic Cleaving Agents of RNA Phosphodiester Linkages. International Journal of Molecular Sciences. 2015; 16(8):17798-17811. https://doi.org/10.3390/ijms160817798
Chicago/Turabian StyleLain, Luigi, Salla Lahdenpohja, Harri Lönnberg, and Tuomas Lönnberg. 2015. "2,6-Bis(1,4,7,10-tetraazacyclododecan-1-ylmethyl)pyridine and Its Benzene Analog as Nonmetallic Cleaving Agents of RNA Phosphodiester Linkages" International Journal of Molecular Sciences 16, no. 8: 17798-17811. https://doi.org/10.3390/ijms160817798