title: 2,5-Anhydro-1-deoxy-1-phosphono-D-altritol, an isosteric analogue of alpha-D-ribofuranose 1-phosphate.
abstract: Condensation of tetramethyl methylenebisphosphonate with 2,3-O-isopropylidene-5-O-trityl-D-ribose gave a mixture of 2,5-anhydro-1-deoxy-1-(diethoxyphosphinyl)-2,3 -O-isopropylidene-5-O-trityl-D-altritol and -allitol. Separation of the isomers and deprotection gave 2,5-anhydro-1-deoxy-1-phosphono-D-altritol and -allitol. The former is the stable isosteric methylenephosphonate analogue of alpha-D-ribose 1-phosphate, the ribose donor in nucleoside phosphorylase catalyzed nucleoside biosynthetic reactions. It did not, however, inhibit purine nucleoside phosphorylase at concentrations of 6 mM.
mesh_terms: D000818:Animals; D002417:Cattle; D006600:Hexosephosphates / Q000138:chemical synthesis* / Q000494:pharmacology; D007536:Isomerism; D010428:Pentosephosphates / Q000138:chemical synthesis / Q000494:pharmacology; D011683:Purine-Nucleoside Phosphorylase / Q000037:antagonists & inhibitors; D012267:Ribosemonophosphates / Q000138:chemical synthesis* / Q000494:pharmacology; D013154:Spleen / Q000201:enzymology
chemical_list: D006600:Hexosephosphates; D010428:Pentosephosphates; D012267:Ribosemonophosphates; C031154:ribose 1-phosphate; C042343:2,5-anhydro-1-deoxy-1-phosphonoaltritol; D011683:Purine-Nucleoside Phosphorylase