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

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dc.contributor.authorMaguire, Nuala M.
dc.contributor.authorFord, Alan
dc.contributor.authorBalzarini, Jan
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderScience Foundation Irelanden
dc.contributor.funderKU Leuvenen
dc.date.accessioned2018-08-13T14:52:32Z
dc.date.available2018-08-13T14:52:32Z
dc.date.issued2018-08-07
dc.date.updated2018-08-13T14:33:54Z
dc.description.abstractThe 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.sponsorshipKU Leuven (University of Leuven (PF-10/018))en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationMaguire, 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.8b01124en
dc.identifier.doi10.1021/acs.joc.8b01124
dc.identifier.endpage21en
dc.identifier.issn0022-3263
dc.identifier.journaltitleThe Journal of Organic Chemistryen
dc.identifier.startpage1en
dc.identifier.urihttps://hdl.handle.net/10468/6600
dc.language.isoenen
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.projectinfo: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.projectinfo: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.projectinfo: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
dc.relation.urihttps://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.8b01124en
dc.subjectPolymerase active siteen
dc.subjectDNA polymeraseen
dc.subjectAlpha-carboxy nucleoside phosphonateen
dc.subjectHerpes virusen
dc.subjectHIVen
dc.subjectReverse transcriptasesen
dc.titleSynthesis of guanine a-carboxy nucleoside phosphonate (G-a-CNP), a direct inhibitor of multiple viral DNA polymerasesen
dc.typeArticle (peer-reviewed)en
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