Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA) |
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| Authors: | Mahesh Kasthuri Laurent Chaloin Christian Périgaud Suzanne Peyrottes |
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| Institution: | 1. IBMM, UMR 5247 CNRS-UM1-UM2, Equipe Nucléosides & Effecteurs Phosphorylés, Université Montpellier 2, cc 1705, place E. Bataillon, 34095 Montpellier, France;2. CPBS, UMR 5236 CNRS-UM1-UM2, Equipe de Biophysique et Bioinformatique, 1919 route de Mende, 34293 Montpellier cedex 5, France |
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| Abstract: | A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside β-ketophosphonate, readily available from the nucleobase and benzylacrylate, afforded a mixture of (R)- and (S)-β-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies and was supported by molecular modelling studies. |
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