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Unlocking P(V): Reagents for chiral phosphorothioate synthesis
Open accessAbstract
A swift citrusy path to chiral phosphorus: The phosphates in the backbones of DNA and RNA are often drawn like crosses but are in fact tetrahedral. Sulfur is sometimes substituted for one of the phosphate oxygens during development of nucleotide-based drugs. Because of the geometry, this swap can lead to two different isomers. Knouse et al. report a pair of phosphorus reagents that conveniently produce either isomer selectively. This ability depended on the configuration of appended limonene substituents that are subsequently jettisoned. In addition to simplifying the route to sulfur-substituted oligonucleotides, these reagents will enable more precise studies of each isomer's distinct bioactivity. Science , this issue p. 1234
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Burdette, D. L., Monroe, K. M., Sotelo-Troha, K., Iwig, J. S., Eckert, B., Hyodo, M., Hayakawa, Y., & Vance, R. E. (2011) · Nature · doi:10.1038/nature10429 · Cited by 1,570
Dunbar, C. E., High, K. A., Joung, J. K., Kohn, D. B., Ozawa, K., & Sadelain, M. (2018) · Science · doi:10.1126/science.aan4672 · Cited by 1,410
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Recent progress in non-native nucleic acid modifications
McKenzie, L. K., El-Khoury, R., Thorpe, J. D., Damha, M. J., & Hollenstein, M. (2021) · Chemical Society Reviews · doi:10.1039/d0cs01430c · Cited by 300
Metadata
- Authors
- Knouse, K. W., deGruyter, J. N., Schmidt, M. A., Zheng, B., Vantourout, J. C., Kingston, C., Mercer, S. E., Mcdonald, I. M., Olson, R. E., Zhu, Y., Hang, C., Zhu, J., Yuan, C., Wang, Q., Park, P., Eastgate, M. D., & Baran, P. S.
- Venue
- Science
- Published
- 2018-09-21
- Volume
- 361
- Issue
- 6408
- Pages
- 1234-1238
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2886572205
- Cited by
- 303
- References
- 2
- FWCI
- 8.16
- Type
- journal article
- Language
- en
- Open access
- green
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- Knouse, K. W., deGruyter, J. N., Schmidt, M. A., Zheng, B., Vantourout, J. C., Kingston, C., Mercer, S. E., Mcdonald, I. M., Olson, R. E., Zhu, Y., Hang, C., Zhu, J., Yuan, C., Wang, Q., Park, P., Eastgate, M. D., & Baran, P. S. (2018). Unlocking P(V): Reagents for chiral phosphorothioate synthesis. Science. https://doi.org/10.1126/science.aau3369
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