[84] - Selective Phosphorylation of Ribonucleosides: Sodium Salt of Guanosine 5′-Phosphate by the Cyanoethyl Dihydrogen Phosphate and Phosphoryl Chloride Methods

Add time:08/28/2019    Source:sciencedirect.com

Publisher SummaryThis chapter discusses the selective phosphorylation of ribonucleosides. Various methods have been proposed for the preparation of ribonucleoside 5'-phosphate. Among them are chemical or enzymic hydrolysis of ribonucleic acid, enzymic phosphorylation of ribonucleosides, and chemical syntheses. However, only chemical syntheses are suitable for preparation on a laboratory scale. Many phosphorylating agents have been proposed for the synthesis of the phosphate esters such as diphenyl phosphorochloridate, dibenzyl phosphorochloridate, tetra-p-nitrophenyl pyrophosphate, phosphoryl chloride (phosphorus oxychloride), and tetrachloropyrophosphoric acid. Among them, 2-cyanoethyl dihydrogen phosphate with DCC is most applicable for the synthesis of nucleoside 5′-phosphates. The cyanoethyl group in the phosphorylated product can be removed easily by mild alkaline hydrolysis. The blocking of the C-2′ and C-3′ hydroxyl groups of the ribonucleoside is done with isopropylidenation, benzylidenation, or acetylation.

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