The Synthesis of 3′-Phosphate and 2′,3′-Cyclic Phosphate of 2-Amino-4-hydroxy-6-(1′,2′,3′-trihydroxypropyl)pteridine
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2-Amino-4-hydroxy-6-(D-<I>erythro</I>-1′,2′,3′-trihydroxypropyl)pteridine 3′-phosphate and 2′,3′-cyclic phosphate, important intermediates of pteridine biosynthesis, were prepared by simple methods. D-<I>erythro</I>-, L-<I>erythro</I>-, D-<I>threo</I>-, and L-<I>threo</I>-isomers of 2-amino-4-hydroxy-6-(1,′,2,′3′-trihydroxypropyl)pteridine, prepared by the method of Viscontini, were phosphorylated with a mixture of phosphorus pentoxide and phosphoric acid. The products were separated by chromatography on a DEAE-cellulose column. The main phosphorylated compounds were 3′-phosphates; small amounts of 2′,3′-diphosphates were also produced. On treatment with DCC, the 3′-phosphate gave 2′,3′-cyclic phosphate.
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