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.

doi:10.1039/c4ra08317b

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.

Authors

L.P. Conway

R.J. Delley

J. Neville

G.R. Freeman

H.J. Maple

V. Chan

A.J. Hall

Professor David Hodgson d.r.w.hodgson@durham.ac.uk
Professor

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