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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. and Mikkola, S. and O’Donoghue, A. C. and 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). pp. 7361-7367.

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+].

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Status:Peer-reviewed
Publisher Web site:http://dx.doi.org/10.1039/C6OB01270A
Publisher statement:This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Date accepted:11 July 2016
Date deposited:12 July 2016
Date of first online publication:11 July 2016
Date first made open access:No date available

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