L.P. Conway
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.
Authors
S. Mikkola
Professor Ann O'Donoghue annmarie.odonoghue@durham.ac.uk
Professor
Professor David Hodgson d.r.w.hodgson@durham.ac.uk
Professor
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 | Jul 12, 2016 |
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 |
Files
Accepted Journal Article
(1.4 Mb)
PDF
Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/
Copyright Statement
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Published Journal Article (Advance online version)
(738 Kb)
PDF
Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/
Copyright Statement
Advance online version
Published Journal Article (Final published version)
(741 Kb)
PDF
Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/
Copyright Statement
Final published version
You might also like
Allophycocyanin A is a carbon dioxide receptor in the cyanobacterial phycobilisome
(2022)
Journal Article
Ubiquitin is a carbon dioxide-binding protein
(2021)
Journal Article
Reactivities of electrophilic N–F fluorinating reagents
(2020)
Journal Article
Kinetics of electrophilic fluorination of steroids and epimerisation of fluorosteroids
(2020)
Journal Article
Downloadable Citations
About Durham Research Online (DRO)
Administrator e-mail: dro.admin@durham.ac.uk
This application uses the following open-source libraries:
SheetJS Community Edition
Apache License Version 2.0 (http://www.apache.org/licenses/)
PDF.js
Apache License Version 2.0 (http://www.apache.org/licenses/)
Font Awesome
SIL OFL 1.1 (http://scripts.sil.org/OFL)
MIT License (http://opensource.org/licenses/mit-license.html)
CC BY 3.0 ( http://creativecommons.org/licenses/by/3.0/)
Powered by Worktribe © 2024
Advanced Search