Synthesis of guanine a-carboxy nucleoside phosphonate (G-a-CNP), a direct inhibitor of multiple viral DNA polymerases

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dc.contributor.author Maguire, Nuala M.
dc.contributor.author Ford, Alan
dc.contributor.author Balzarini, Jan
dc.contributor.author Maguire, Anita R.
dc.date.accessioned 2018-08-13T14:52:32Z
dc.date.available 2018-08-13T14:52:32Z
dc.date.issued 2018-08-07
dc.identifier.citation Maguire, N. M., Ford, A., Balzarini, J. and Maguire, A. R. (2018) 'Synthesis of Guanine α-Carboxy Nucleoside Phosphonate (G-α-CNP), a direct inhibitor of multiple viral DNA polymerases', The Journal of Organic Chemistry, In Press, doi:10.1021/acs.joc.8b01124 en
dc.identifier.startpage 1 en
dc.identifier.endpage 21 en
dc.identifier.issn 0022-3263
dc.identifier.uri http://hdl.handle.net/10468/6600
dc.identifier.doi 10.1021/acs.joc.8b01124
dc.description.abstract The synthesis of guanine α-carboxy nucleoside phosphonate (G-α-CNP) is described. Two routes provide access to racemic G-α-CNP 9, one via base construction and the other utilizing Tsuji–Trost allylic substitution. The latter methodology was also applied to the enantiopure synthesis of both antipodes of G-α-CNP, each of which shows interesting antiviral DNA polymerase activity. Additionally, we report an improved multi-gram scale preparation of the cyclopentene building block 10, starting material for the preferred Tsuji–Trost route to 9. en
dc.description.sponsorship KU Leuven (University of Leuven (PF-10/018)) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher American Chemical Society (ACS) en
dc.relation.uri https://pubs.acs.org/doi/abs/10.1021/acs.joc.8b01124
dc.rights © American Chemical Society. This document is the Accepted Manuscript version of a Published Work that will appear in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acs.joc.8b01124 en
dc.subject Polymerase active site en
dc.subject DNA polymerase en
dc.subject Alpha-carboxy nucleoside phosphonate en
dc.subject Herpes virus en
dc.subject HIV en
dc.subject Reverse transcriptases en
dc.title Synthesis of guanine a-carboxy nucleoside phosphonate (G-a-CNP), a direct inhibitor of multiple viral DNA polymerases en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Anita Maguire, Vice President For Research, University College Cork, Cork, Ireland. +353-21-490-3000 Email: a.maguire@ucc.ie en
dc.internal.availability Full text available en
dc.check.info Access to this article is restricted until 12 months after publication by request of the publisher. en
dc.check.date 2019-08-07
dc.date.updated 2018-08-13T14:33:54Z
dc.description.version Accepted Version en
dc.internal.rssid 449387512
dc.contributor.funder Science Foundation Ireland en
dc.contributor.funder KU Leuven en
dc.description.status Peer reviewed en
dc.identifier.journaltitle The Journal of Organic Chemistry en
dc.internal.copyrightchecked No !!CORA!! en
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress a.maguire@ucc.ie en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/05/PICA/B802 TIDA 09/IE/Powder diffraction of pharmaceutical co-crystals/ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Principal Investigator Programme (PI)/05/PICA/B802/IE/Design and Synthesis of Novel Phosphononucleosides - Potential Antiviral Agents/ en
dc.relation.project info:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/14/TIDA/2402/IE/Synthesis and biological evaluation of prodrug derivatives of _-carboxynucleosidephosphonate NRTIs (_ -CNPs)/ en


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