ArticleBiochemistry2009
Ambivalent incorporation of the fluorescent cytosine analogues tC and tCo by human DNA polymerase alpha and Klenow fragment.
Article in Biochemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Increased brightness of fluorescent uridine, qU, inside single- and double-stranded RNA.Scientific reports · 2026Article
- Dual chemical labeling enables nucleotide-resolution mapping of DNA abasic sites and common alkylation damage in human mitochondrial DNA.Nucleic acids research · 2023Article
- Stealth Fluorescence Labeling for Live Microscopy Imaging of mRNA Delivery.Journal of the American Chemical Society · 2021Article
- Single-Molecule Detection of a Fluorescent Nucleobase Analogue via Multiphoton Excitation.The journal of physical chemistry letters · 2019Article
- Article
- Synthesis and polymerase activity of a fluorescent cytidine TNA triphosphate analogue.Nucleic acids research · 2017Article
- Conformational Dynamics of DNA Repair by Escherichia coli Endonuclease III.The Journal of biological chemistry · 2015Article
- Functionalized tricyclic cytosine analogues provide nucleoside fluorophores with improved photophysical properties and a range of solvent sensitivities.Chemistry (Weinheim an der Bergstrasse, Germany) · 2014Article
- New environment-sensitive multichannel DNA fluorescent label for investigation of the protein-DNA interactions.PloS one · 2014Article
- Using a fluorescent cytosine analogue tC(o) to probe the effect of the Y567 to Ala substitution on the preinsertion steps of dNMP incorporation by RB69 DNA polymerase.Biochemistry · 2012Article
- Synthetic nucleotides as probes of DNA polymerase specificity.Journal of nucleic acids · 2012Article
- Effect of transition metal ions on the fluorescence and Taq-catalyzed polymerase chain reaction of tricyclic cytidine analogs.Analytical biochemistry · 2011Article
- Substitution of Ala for Tyr567 in RB69 DNA polymerase allows dAMP and dGMP to be inserted opposite Guanidinohydantoin .Biochemistry · 2010Article
- Site-specific fluorescent probing of RNA molecules by unnatural base-pair transcription for local structural conformation analysis.Nature protocols · 2010Article
- Mechanisms by which human DNA primase chooses to polymerize a nucleoside triphosphate.Biochemistry · 2010Article
- Incorporation of the fluorescent ribonucleotide analogue tCTP by T7 RNA polymerase.Analytical chemistry · 2010Article
- High density labeling of polymerase chain reaction products with the fluorescent base analogue tCo.Analytical chemistry · 2009Article
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Authors and funding
5 authors.
Funding
Abstract
We studied the incorporation of the fluorescent cytidine analogues 1,3-diaza-2-oxophenothiazine (tC) and 1,3-diaza-2-oxophenoxazine (tCo) by human DNA polymerase alpha and Klenow fragment of DNA polymerase I (Escherichia coli). These tricyclic nucleobases possess the regular hydrogen bonding interface of cytosine but are significantly expanded in size toward the major groove. Despite the size alteration, both DNA polymerases insert dtCTP and dtCoTP with remarkable catalytic efficiency. Polymerization opposite guanine is comparable to the insertion of dCTP, while the insertion opposite adenine is only approximately 4-11 times less efficient than the formation of a T-A base pair. Both enzymes readily extend the formed tC(o)-G and tC(o)-A base pairs and can incorporate at least four consecutive nucleotide analogues. Consistent with these results, both DNA polymerases efficiently polymerize dGTP and dATP when tC and tCo are in the template strand. Klenow fragment inserts dGTP with a 4-9-fold higher probability than dATP, while polymerase alpha favors dGTP over dATP by a factor of 30-65. Overall, the properties of tC(o) as a templating base and as an incoming nucleotide are surprisingly symmetrical and may be universal for A and B family DNA polymerases. This finding suggests that the aptitude for ambivalent base pairing is a consequence of the electronic properties of tC(o).
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