PMID: 9443970Mar 14, 1998Paper

2'-Deoxynucleoside 5'-triphosphates modified at alpha-, beta- and gamma-phosphates as substrates for DNA polymerases

Nucleic Acids Research
Ludmila AlexandrovaA A Krayevsky

Abstract

Replacement of alpha-, beta- and gamma-phosphate groups in 2'-deoxynucleoside 5'-triphosphates (dNTP) with phosphonate groups yields a new set of dNTP mimics with potential biological and therapeutic applications. Here, we describe the synthesis of 15 new dNTPs modified at alpha-, beta- and gamma-phosphates containing, in the case of dUTP, reporter and ligand groups at the C5 position of uracil. It was shown that gamma-substituted dNTPs were substrates for AMV reverse transcriptase despite of the large size of substituent at the gamma-phosphonate. On the other hand, these compounds were poorly utilized by DNA polymerase alpha. For dUTP analogues substituted at both gamma-phosphonate and C5 of uracil, the substrate affinity was 1-2 orders of magnitude lower than for their counterparts containing substituents either at gamma-phosphonate or C5 position. Meanwhile, C5-substituted beta, gamma-dibromomethylenediphosphonates demonstrated poor activity or were not active at all as substrates for AMV reverse transcriptase. Finally, 2'-deoxythymidine 5'-[beta, gamma-(methylphosphinyl)methylphosphonyl]-alpha-phosphate and its 3'-azido-3'-deoxy analog were substrates for AMV reverse transcriptase, but the substrate activity of these analog...Continue Reading

References

Feb 25, 1992·Nucleic Acids Research·L S VictorovaM K Kukhanova
Oct 4, 1996·The Journal of Biological Chemistry·A A ArzumanovA A Krayevsky

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Citations

Nov 23, 2007·Journal of the American Chemical Society·Charles E McKennaSamuel H Wilson
May 5, 2007·Nucleosides, Nucleotides & Nucleic Acids·Maxim JaskoMarina Kukhanova
Feb 10, 2000·Nucleic Acids Research·A A ArzumanovA A Krayevsky
Jul 27, 2001·Nucleic Acids Research·K VastmansP Herdewijn
Nov 14, 2008·Chembiochem : a European Journal of Chemical Biology·Marleen RendersPiet Herdewijn
Jul 31, 2013·Bioorganic & Medicinal Chemistry·Eduard R ShmalenyukLudmila A Alexandrova
Jul 14, 1999·FEBS Letters·L VictorovaA Krayevsky
Jun 5, 2010·Viruses·Antonio J Acosta-Hoyos, Walter A Scott
Apr 14, 2012·Bioorganicheskaia khimiia·L A Aleksandrova
Jan 15, 2020·The Journal of Antibiotics·Sergey D NegryaLiudmila A Alexandrova
Oct 31, 2007·Chemical Reviews·Ping LiBarbara Ramsay Shaw

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