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In this process, the first phosphorylation step, catalysed by nucleoside monophosphate kinases (NMP kinases), has been proposed as a bottleneck. Herein, we report the synthesis of a series of ribonucleoside phosphonate derivatives isosteric to 5\u2032\u2010mononucleotides, with different degrees of flexibility within the 5\u2032,6\u2032\u2010C\uf8ffC bond, as well as different polarities, through the introduction of hydroxy groups. The influence of these modifications on the capacity of the compounds to act as substrates for appropriate human NMP kinases, involved in nucleic acids metabolism, has been investigated. Low flexibility, as well as an absence of hydroxy groups within the ribose\u2013phosphorus architecture, is critical for efficient phosphotransfer. Among the series of pyrimidine analogues, one derivative was shown to be phosphorylated by human UMP\u2010CMP kinase, with rates similar to those of dUMP and even better than dCMP.<\/jats:p>","DOI":"10.1002\/cmdc.201100068","type":"journal-article","created":{"date-parts":[[2011,5,12]],"date-time":"2011-05-12T12:16:56Z","timestamp":1305202616000},"page":"1094-1106","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["5\u2032,6\u2032\u2010Nucleoside Phosphonate Analogues Architecture: Synthesis and Comparative Evaluation towards Metabolic Enzymes"],"prefix":"10.1002","volume":"6","author":[{"given":"Franck","family":"Gallier","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julie A. 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