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Issue 8, 2011
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Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate

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Abstract

The synthesis of the novel nucleotide analogues 5′-deoxynucleoside-5′-S-methylphosphonates, starting from 5′-deoxy-5′-haloribonucleosides, 5′-O-tosylribonucleosides, and 2′-O-triflylnucleosides, is described. The phosphonothiolation of these compounds was achieved using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new, odourless, and efficient equivalent of mercaptomethylphosphonate. The thiolate anion of mercaptomethylphosphonate was generated in situ from the isothiouronium salt in both protic and aprotic solvents using two equivalents of sodium iso-propoxide. The prepared nucleoside 5′-S-methylphosphonates were deprotected, and the free phosphonic acids were transformed into diphosphoryl derivatives (the NTP analogues). Both mononucleotides and NTP analogues were studied as substrates/inhibitors of several enzymes that are involved in the nucleoside/nucleotide metabolism.

Graphical abstract: Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate

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Publication details

The article was received on 17 Sep 2010, accepted on 06 Jan 2011 and first published on 02 Mar 2011


Article type: Paper
DOI: 10.1039/C0OB00738B
Citation: Org. Biomol. Chem., 2011,9, 2856-2860
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    Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate

    I. Kóšiová, M. Buděšínský, N. Panova and I. Rosenberg, Org. Biomol. Chem., 2011, 9, 2856
    DOI: 10.1039/C0OB00738B

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