Trityl chloride → HCID 136332169, compound

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Reaction Steps

Guanosine 3'-monophosphate (3'-GMP), a compound of formula (I) in which Y is H2PO3 and X and Z are hydrogen atoms, and guanosine 2'-monophosphate (2'-GMP), a compound of formula (I) in which X is H2PO3 and Z and Y are hydrogen atoms, can be obtained in the following manner in accordance with the method of Brown and Todd [D. M. Brown and A. R. Todd, J. Chem. Soc., 44 (1952)]. Specifically, guanosine and trityl chloride are reacted in anhydrous pyridine at 60° C. for 3 days to obtain 5'-tritylguanosine as a result of selective tritylation of the 5'-position. The resulting 5'-tritylguanosine is dissolved in pyridine, and while cooling the solution at -20° C., diphenylphosphoryl chloride was added to obtain a mixture of a trityl derivative of 2'-monophosphate of guanosine and 3'-monophosphate of guanosine. The mixture is dissolved in 80% acetic acid, and the solution is heated under reflux to remove the trityl group to obtain a mixture of 2'-GMP and 3'-GMP. The mixture is charged onto a column of Dowex 1® (formic acid type). The column is eluted with 0.1N formic acid to obtain guanosine 2'-monophosphate as an eluate, and with 1N formic acid to obtain guanosine 3'-monophosphate as an eluate. These eluates are each concentrated, lyophilized and recrystallized from water to separate the desired 2'-GMP and 3'-GMP.

Provenance & Evidence