ArticleJournal of medicinal chemistry2008
Alpha,beta-methylene-2'-deoxynucleoside 5'-triphosphates as noncleavable substrates for DNA polymerases: isolation, characterization, and stability studies of novel 2'-deoxycyclonucleosides, 3,5'-cyclo-dG, and 2,5'-cyclo-dT.
Article in Journal of medicinal chemistry, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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6 citing papers in PubMed, 15 citations in OpenAlex.
- Cap analogs with a hydrophobic photocleavable tag enable facile purification of fully capped mRNA with various cap structures.Nature communications · 2023Article
- Highly potent and selective ectonucleotide pyrophosphatase/phosphodiesterase I inhibitors based on an adenosine 5'-(α or γ)-thio-(α,β- or β,γ)-methylenetriphosphate scaffold.Journal of medicinal chemistry · 2014Article
- Insights into the conformation of aminofluorene-deoxyguanine adduct in a DNA polymerase active site.The Journal of biological chemistry · 2013Article
- Stereospecific formation of a ternary complex of (S)-α,β-fluoromethylene-dATP with DNA pol β.Chembiochem : a European journal of chemical biology · 2012Article
- Bisubstrate adenylation inhibitors of biotin protein ligase from Mycobacterium tuberculosis.Chemistry & biology · 2011Article
- DNA polymerase beta ribonucleotide discrimination: insertion, misinsertion, extension, and coding.The Journal of biological chemistry · 2010Article
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Authors and funding
8 authors at 3 institutions in 1 country.
Funding
Abstract
We report synthesis and characterization of a complete set of alpha,beta-methylene-2'-dNTPs (alpha,beta-m-dNTP; N = A, C, T, G, 12-15) in which the alpha,beta-oxygen linkage of natural dNTP was replaced by a methylene group. These nucleotides were designed to be noncleavable substrates for DNA polymerases. Synthesis entails preparation of 2'-deoxynucleoside 5'-diphosphate precursors, followed by an enzymatic gamma-phosphorylation. All four synthesized alpha,beta-m-dNTPs were found to be potent inhibitors of polymerase beta, with K i values ranging 1-5 microM. During preparation of the dG and dT derivatives of alpha,beta-methylene diphosphate, we also isolated significant amounts of 3,5'-cyclo-dG (16) and 2,5'-cyclo-dT (17), respectively. These novel 2'-deoxycyclonucleosides were formed via a base-catalyzed intramolecular cyclization (N3 --> C5' and O2 --> C5', respectively). In acidic solution, both 16 and 17 underwent glycolysis, followed by complete depurination. When exposed to alkaline conditions, 16 underwent an oxidative deamination to produce 3,5'- cyclo-2'-deoxyxanthosine (19), whereas 17 was hydrolyzed exclusively to dT.
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