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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

1988; Oxford University Press; Volume: 61; Issue: 9 Linguagem: Inglês

10.1246/bcsj.61.3217

1348-0634

Yoshisuke Yamamoto, Yoshinobu Baba, Miwa Mizokuchi, Mika Onoe, Tomoko Sumiyama, Mitsutomo Tsuhako, Norimasa Yoza, Shigeru Ohashi,

Bone health and treatments

Abstract 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.