The Aqueous N-Phosphorylation and N-Thiophosphorylation of Aminonucleosides

Conway, L.P.; Delley, R.J.; Neville, J.; Freeman, G.R.; Maple, H.J.; Chan, V.; Hall, A.J.; Hodgson, D.R.W.

Abstract

We demonstrate N-phosphorylation and N-thiophosphorylation of unprotected aminonucleosides in aqueous media. N-Phosphorylations using phosphoric chloride and N-thiophosphorylations using thiophosphoryl chloride were explored as functions of pH using 5′-amino-5′-deoxyguanosine as substrate. These reagents were compared to phosphodichloridate and thiophosphodichloridate ions, and the methodology was applied to other aminonucleosides. S-Alkylations of the nucleoside N-thiophosphoramidates were investigated as functions of pH and alkylating agent.

Citation

Conway, L., Delley, R., Neville, J., Freeman, G., Maple, H., Chan, V., …Hodgson, D. (2014). The Aqueous N-Phosphorylation and N-Thiophosphorylation of Aminonucleosides. RSC Advances, 2014(73), 38663-38671. https://doi.org/10.1039/c4ra08317b

• Journal Article Type: Article
• Publication Date: Aug 27, 2014
• Deposit Date: Aug 11, 2014
• Publicly Available Date: Sep 18, 2014
• Journal: RSC Advances
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 2014
• Issue: 73
• Pages: 38663-38671
• DOI: https://doi.org/10.1039/c4ra08317b
• Public URL: https://durham-repository.worktribe.com/output/1446900