Toti, Kiran

Van Calenbergh, Serge

English

Ghent University Academic Bibliography

Synthesis of L-2-Deoxythreose Nucleosides as Potential Antiviral Agents  Kiran S. Toti and Serge Van Calenbergh*   Laboratory for Medicinal Chemistry (FFW), Ghent University, Harelbekestraat 72, 9000 Gent, Belgium.   L-2-deoxythreose nucleoside phosphonates are known to selectively inhibit HIV without affecting human DNA synthesis.1 These nucleoside analogues require two additional phosphorylation steps by cellular kinases before they are incorporated in the viral genome and lead to chain termination.  It is believed that a cis orientation of the base and the 3’-substituent is a structural requirement for optimal conversion to the diphosphate. Inspired by these findings, we decided to explore the antiviral properties of the threose-based nucleoside analogues, which are anticipated to have superior bioavailability compared to the parent phosphonates.   The synthesis of analogs involving a Vorbrüggen coupling and a Barton-McCombie deoxygenation, will be described.  Reference: 1. Wu et al. J. Am. Chem. Soc. (2005), 127, 5056-5065.   OHOBR = Bn/ PMBB  = Natural/  Modified        NucleobasesOOOORVorbrüggen CouplingBarton-McCombie   DeoxygenationDeprotection

Synthesis of L-2-deoxythreose nucleosides as potential antiviral agents

https://biblio.ugent.be/publication/3063459/file/3063460.pdf

Synthesis of L-2-deoxythreose nucleosides as potential antiviral agents

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Ghent University Academic Bibliography