Description
A oxopurine that is adenine bearing a single oxo substituent at position 8.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C5H5N5O | 0 | 151.126 |
Recommended notation
| Name | 8-oxoadenine |
|---|---|
| Abbreviation | 8oxoA |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey | Synonyms |
|---|---|---|---|---|
| 6-amino-1,7-dihydro-8H-purin-8-one | C=12C(=NC=NC1N)NC(N2)=O | InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-3)10-5(11)9-2/h1H,(H4,6,7,8,9,10,11) | RGKBRPAAQSHTED-UHFFFAOYSA-N |
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Mapping techniques
| Method |
Method detail
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Resolution
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Qualifier
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References |
|---|---|---|---|---|
| SMRT | direct detection | single-base | target sequences |
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Citations
- Barone, F, et al. 2001. Influence of an 8-oxoadenine lesion on the structural and dynamic features of a 30-mer DNA fragment with and without a mismatch. International Journal of Radiation Biology. 78(1).
- Bespalov, IA, et al. 1996. Recombinant Phabs reactive with 7,8-dihydro-8-oxoguanine, a major oxidative DNA lesion. Biochemistry. 35(7).
- Biggadike, K, et al. 2016. Discovery of 6-Amino-2-{[(1S)-1-methylbutyl]oxy}-9-[5-(1-piperidinyl)pentyl]-7,9-dihydro-8H-purin-8-one (GSK2245035), a Highly Potent and Selective Intranasal Toll-Like Receptor 7 Agonist for the Treatment of Asthma. Journal of Medicinal Chemistry. 59(5).
- Clark, TA, et al. 2011. Direct detection and sequencing of damaged DNA bases. Genome Integrity. 2.
- Duplaa, AM, et al. 1989. Measurement of the radiosensitivity of a radiation-induced adenine defect in a single stranded DNA chain. Radiation and Environmental Biophysics. 28(3).
- Girard, PM, et al. 1998. Opposite base-dependent excision of 7,8-dihydro-8-oxoadenine by the Ogg1 protein of Saccharomyces cerevisiae. Carcinogenesis. 19(7).
- Guschlbauer, W, et al. 1991. Structure and in vitro replication of DNA templates containing 7,8-dihydro-8-oxoadenine. Nucleic Acids Research. 19(8).
- Jałoszyński, P, et al. 2003. Oxidative DNA base modifications and polycyclic aromatic hydrocarbon DNA adducts in squamous cell carcinoma of larynx. Free Radical Research. 37(3).
- Jensen, A, et al. 2003. Mammalian 8-oxoguanine DNA glycosylase 1 incises 8-oxoadenine opposite cytosine in nuclei and mitochondria, while a different glycosylase incises 8-oxoadenine opposite guanine in nuclei. The Journal of Biological Chemistry. 278(21).
- Jetter, MC, et al. 1993. 7,8-Dihydro-8-oxoadenine as a replacement for cytosine in the third strand of triple helices. Triplex formation without hypochromicity. Biochemistry. 32(13).
- Konvalinová, H, et al. 2015. Diverse effects of naturally occurring base lesions on the structure and stability of the human telomere DNA quadruplex. Biochimie. 118.
- Nakamura, T, et al. 2012. Synthesis and evaluation of 8-oxoadenine derivatives as potent Toll-like receptor 7 agonists with high water solubility. Bioorganic & Medicinal Chemistry Letters. 23(3).
- Sekine, M, et al. 2004. Structure-activity relationship of phosmidosine: importance of the 7,8-dihydro-8-oxoadenosine residue for antitumor activity. Bioorganic & Medicinal Chemistry. 12(19).
- Strohmeier, J, et al. 2011. Changing nucleotide specificity of the DEAD-box helicase Hera abrogates communication between the Q-motif and the P-loop. Biological Chemistry. 392(4).
- Talhaoui, I, et al. 2012. 7,8-Dihydro-8-oxoadenine, a highly mutagenic adduct, is repaired by Escherichia coli and human mismatch-specific uracil/thymine-DNA glycosylases. Nucleic Acids Research. 41(2).
- Talhaoui, I, et al. 2014. Aberrant repair initiated by mismatch-specific thymine-DNA glycosylases provides a mechanism for the mutational bias observed in CpG islands. Nucleic Acids Research. 42(10).
- Terashima, Y, et al. 2000. Further studies of KMnO4 oxidation of synthetic DNAs containing oxidatively damaged bases. Nucleic Acids Symposium Series. (42).
- Yim, JJ, et al. 2015. Nematode signaling molecules derived from multimodular assembly of primary metabolic building blocks. Organic Letters. 17(7).