Summary
1. The methyl esters of thymidylyl-(5′→N)-and thymidylyl-(3′→N)-phenylalanines have been obtained from the mixed anhydrides of the corresponding nucleotides with diphenyl phosphate with yields of 50–60%.
2. The esters of the thymidylyl-(P→N)- phenylalanines are readily hydrolyzed in an acid medium. The phosphoramide bond in the thymidylylphenylalanines is stable in the pH range from 4 to 12.
3. The conversion of the ester of thymidylyl-(3′→N)-phenylalanine into thymidine-3′, 5′ cyclic phosphate shows the ease of protonation of the amide nitrogen with the participation of the 5′-hydroxyl group and subsequent nucleophilic substitution on the nucleotidic phosphorus atom.
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References
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Khimiya Prirodnykh Soedinenii, Vol. 2, No. 1, pp. 35–39, 1966
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Bakanova, V.A., Shabarova, Z.A. & Prokof'ev, M.A. Synthesis and properties of thymidylyl-(P → N) phenylalanines. Chem Nat Compd 2, 28–31 (1966). https://doi.org/10.1007/BF00566596
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DOI: https://doi.org/10.1007/BF00566596