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• W2100090745 abstract "Several 2′-deoxythymidine 5′-triphosphate and 3′-azido-2′,3′-dideoxythymidine 5′-triphosphate analogs containing a hydrophobic phosphonate group instead of the γ-phosphate were synthesized and evaluated as substrates for human immunodeficiency virus (HIV) and avian myeloblastosis virus reverse transcriptases, human placental DNA polymerases α and β, and calf thymus terminal deoxynucleotidyl transferase. They were efficiently incorporated into the DNA chain by the retroviral enzymes but were not utilized by the mammalian ones. Also, some γ-ester and γ-amide derivatives of dTTP and 3′-azido-2′,3′-dideoxythymidine 5′-triphosphate (AZTTP) were synthesized and studied. They proved to be substrates for both the retroviral and mammalian enzymes under study. The Km values for incorporation of the dTTP derivatives into the DNA chain were close to those for dTTP and AZTTP. The Km for the AZTTP derivatives were one order of magnitude greater than those for dTTP and AZTTP. The results obtained indicate that HIV and avian myeloblastosis virus reverse transcriptases have no sterical obstacles for binding the triphosphate fragment bearing a bulky substituent at the γ-position. Modification of the γ-phosphate in AZTTP increased the selectivity of HIV reverse transcriptase inhibition versus DNA polymerase α. γ-Methylphosphonate and γ-phenylphosphonate were dephosphorylated in human serum much less rapidly than AZTTP. Besides, they were shown to be markedly more hydrophobic than AZTTP. Thus, replacement of the γ-phosphate in AZTTP with γ-phosphonate markedly alters its substrate properties toward some cellular DNA polymerases and blood dephosphorylating enzymes but does not change its substrate activity with respect to HIV reverse transcriptase. Several 2′-deoxythymidine 5′-triphosphate and 3′-azido-2′,3′-dideoxythymidine 5′-triphosphate analogs containing a hydrophobic phosphonate group instead of the γ-phosphate were synthesized and evaluated as substrates for human immunodeficiency virus (HIV) and avian myeloblastosis virus reverse transcriptases, human placental DNA polymerases α and β, and calf thymus terminal deoxynucleotidyl transferase. They were efficiently incorporated into the DNA chain by the retroviral enzymes but were not utilized by the mammalian ones. Also, some γ-ester and γ-amide derivatives of dTTP and 3′-azido-2′,3′-dideoxythymidine 5′-triphosphate (AZTTP) were synthesized and studied. They proved to be substrates for both the retroviral and mammalian enzymes under study. The Km values for incorporation of the dTTP derivatives into the DNA chain were close to those for dTTP and AZTTP. The Km for the AZTTP derivatives were one order of magnitude greater than those for dTTP and AZTTP. The results obtained indicate that HIV and avian myeloblastosis virus reverse transcriptases have no sterical obstacles for binding the triphosphate fragment bearing a bulky substituent at the γ-position. Modification of the γ-phosphate in AZTTP increased the selectivity of HIV reverse transcriptase inhibition versus DNA polymerase α. γ-Methylphosphonate and γ-phenylphosphonate were dephosphorylated in human serum much less rapidly than AZTTP. Besides, they were shown to be markedly more hydrophobic than AZTTP. Thus, replacement of the γ-phosphate in AZTTP with γ-phosphonate markedly alters its substrate properties toward some cellular DNA polymerases and blood dephosphorylating enzymes but does not change its substrate activity with respect to HIV reverse transcriptase." @default.
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• W2100090745 date "1996-10-01" @default.
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• W2100090745 title "γ-Phosphate-substituted 2′-Deoxynucleoside 5′-Triphosphates as Substrates for DNA Polymerases" @default.
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• W2100090745 doi "https://doi.org/10.1074/jbc.271.40.24389" @default.
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