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The Synthesis, Conformation and Hydrolytic Stability of an N,S-bridging Thiophosphoramidate Analogue of Thymidylyl-3ʹ,5ʹ-Thymidine

Conway, L.P.; Mikkola, S.; O’Donoghue, A.C.; Hodgson, D.R.W.

The Synthesis, Conformation and Hydrolytic Stability of an N,S-bridging Thiophosphoramidate Analogue of Thymidylyl-3ʹ,5ʹ-Thymidine Thumbnail


Authors

L.P. Conway

S. Mikkola



Abstract

A 3'-N,5'-S-bridging thiophosphoramidate analogue of thymidylyl-3ʹ,5ʹ-thymidine was synthesised under aqueous conditions. 1H NMR conformational measurements show that the 3'-N-substituted deoxyribose ring is biased towards the 'north', RNA-like conformation. Rate constants for hydrolysis of the analogue were measured at 90 °C in the pH range 1.3-10.9. The pH-log kobs profile displays a pH-independent region between approximately pH 7 and 10 (t½ ~13 days). Under acidic conditions, kobs displays a first order dependence on [H3O+].

Citation

Conway, L., Mikkola, S., O’Donoghue, A., & Hodgson, D. (2016). The Synthesis, Conformation and Hydrolytic Stability of an N,S-bridging Thiophosphoramidate Analogue of Thymidylyl-3ʹ,5ʹ-Thymidine. Organic and Biomolecular Chemistry, 14(30), 7361-7367. https://doi.org/10.1039/c6ob01270a

Journal Article Type Article
Acceptance Date Jul 11, 2016
Online Publication Date Jul 11, 2016
Publication Date Aug 14, 2016
Deposit Date May 26, 2016
Publicly Available Date Mar 29, 2024
Journal Organic and Biomolecular Chemistry
Print ISSN 1477-0520
Electronic ISSN 1477-0539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 14
Issue 30
Pages 7361-7367
DOI https://doi.org/10.1039/c6ob01270a

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