Abstract
THE recent announcement1 that 5-iodo-2′-deoxyuridine (IUDR) is effective against the herpes simplex virus, whereas the riboside, 5-iodo-uridine, is not, emphasizes the possible therapeutic differences between ribosides and 2′-deoxyribosides of a common heterocyclic base. As a result of our interest in preparing potentially better forms of certain common antitumour drugs, we have recently reported the synthesis of the 2′-deoxyriboside of 6-mercaptopurine2; we now describe the synthesis of 2′-deoxythioguanosine (DTG). In view of LePage's report3 that the tumour-inhibitory properties of 6-thioguanine result from the incorporation of this guanine analogue into the nucleic acids (probably specifically the DNA), DTG is of especial interest since it represents the closest practical precursor of thioguanine as it is incorporated in the DNA; it by-passes some of the steps from thioguanine to its incorporation into DNA.
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IWAMOTO, R., ACTON, E. & GOODMAN, L. 2′-Deoxythioguanosine and its α-Anomer. Nature 198, 285 (1963). https://doi.org/10.1038/198285a0
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DOI: https://doi.org/10.1038/198285a0
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