Phosphonylation of biomolecules with inorganic diphosphonate. II. Phosphonylation of phosphate groups on nucleoside 5'-monophosphates, deoxynucleoside 5'-monophosphates, and sugar phosphates.

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  • Phosphonylation of Biomolecules with Inorganic Diphosphonate. II. Phosphonylation of Phosphate Groups on Nudeoside 5′-Monophosphates, Deoxynudeoside 5′-Monophosphates, and Sugar Phosphates

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Inorganic diphosphonate phosphonylated predominantly phosphate groups on nucleoside 5′-monophosphates (=NMP’s: AMP, GMP, IMP, CMP, and UMP), deoxynudeoside 5′-monophosphates (=dNMP’s: dAMP and dTMP), and sugar phosphates (=SP’s: GlclP, Glc6P, and Rib5P) in aqueous solutions under mild conditions (50–70 °C, pH 6). The chemical structures of phosphonylated products were discussed on their 31P NMR spectra and high-performance liquid chromatograms. The main phosphonylated products from NMP’s and dNMP’s were analogous in structure to nucleoside 5′-diphosphates. The rate of phosphonylation of phosphate groups on NMP’s, dNMP’s, and SP’s varied strongly depending on reaction conditions: pH, reaction temperature, and initial concentration of inorganic diphosphonate. The maximum yields of phosphonylated products were ca. 70% for all NMP’s, dNMP’s, and SP’s under the following conditions: initial concentration of inorganic diphosphonate is 1.5 mol dm−3; each initial concentration of NMP’s, dNMP’s, or SP’s is 0.1 mol dm−3; 70 °C; pH 6.

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