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Durham University

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Publication details for Dr David R.W. Hodgson

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

Author(s) from Durham


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+].