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

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) deriv...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-11, Vol.22 (44), p.8737-8742
Main Authors: Jastrz bska, Katarzyna, Anto czyk, Patrycja, Dolot, Rafa
Format: Article
Language:English
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Summary: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 ( m U-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.
ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d4ob01437e