P-Stereodefined morpholino dinucleoside 3′,5′-phosphorothioates†

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Authors
Jastrzębska, Katarzyna ORCID logo 0000-0003-3979-3186
Antończyk, Patrycja
Dolot, Rafał
Date
2024-10-11
Journal Title
Journal ISSN
Volume Title
Publisher
The Royal Society of Chemistry
License
Creative Commons License
Creative Commons Attribution-NonCommercial 3.0 Unported License
Abstract
Here, we present for the first time the synthesis of P-stereodefined morpholino phosphorothioate analogs by using a modified 1,3,2-oxathiaphospholane method (OTP method) and provide valuable structural insights into their stereochemistry. N-(2-Thio-4,4-pentamethylene-1,3,2-oxathiaphospholane) derivatives of morpholino-type nucleosides (mU-OTPs) were synthesized, separated into pure P-diastereomers and used to prepare P-stereodefined morpholino dinucleoside 3 ',5 '-phosphorothioates. We present P-stereodefined morpholino phosphorothioate analogs and provide valuable structural insights into their stereochemistry. These P-diastereomerically pure analogs could have a significant impact in the field of nucleic acid therapeutics.
Description
Keywords
stereocontrolled synthesis    thermal-stability    duplexes
Citation
Jastrzębska, K., Antończyk, P, Dolot, R. (2024). P-Stereodefined morpholino dinucleoside 3′,5′-phosphorothioates†. Organic & Biomolecular Chemistry, 22(44), 8737-8742. DOI https://doi.org/10.1039/D4OB01437E
URI
https://open.icm.edu.pl/handle/123456789/25572
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