Publication details for Dr David R.W. HodgsonConway, 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.
- Publication type: Journal Article
- ISSN/ISBN: 1477-0520, 1477-0539
- DOI: 10.1039/C6OB01270A
- Further publication details on publisher web site
- Durham Research Online (DRO) - may include full text
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+].