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Chemical Compound Review:

IGA 6-amino-1,7-dihydropurin-2-one

Synonyms: Isoguanine, PubChem9258, CHEMBL506639, SureCN134675, SureCN134676, ...

Sherrill, C.B. et al., Rogstad, K.N. et al., Sismour, A.M. et al., Switzer, C.Y. et al., Qin, X. et al., et al.

Sismour, Benner,

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High impact information on Isoguanine

Using the previously described nonstandard DNA base pair constructed from isoguanine and 5-methylisocytosine, we report a highly specific and sensitive method that allows for the fast and specific quantitation of genetic sequences in a closed tube format [1].
In this paper, we investigate two purines that could arise by endogenous damage of the normal DNA bases: isoguanine (which can be generated by the oxidation of adenine) and xanthine (which can be generated by the deamination of guanine) [2].
Isoguanine analogues 11a-d lacked antiviral activity but pronucleotides 11c,d were substrates for porcine liver esterase [3].
To test whether this might allow PCR amplification of a six-letter artificially expanded genetic information system, we examined the relative rates of misincorporation of 2-thioTTP and TTP opposite isoG using affinity electrophoresis [4].
2-Hydroxyadenine (isoguanine) as oxidative DNA damage: its formation and mutation inducibility [5].

Associations of Isoguanine with other chemical compounds

The ability of various polymerases to catalyze the template-directed formation of a base pair between isoguanine (iso-G) and isocytosine (iso-C) in duplex oligonucleotides has been investigated [6].
New base pairs between isoguanine or guanine and 5-aza-7-deazaguanine are presented [7].

Analytical, diagnostic and therapeutic context of Isoguanine

During PCR amplification, enzymatic site-specific incorporation of a quencher covalently linked to isoguanine allows for the simultaneous detection and identification of multiple targets [1].

References

Nucleic acid analysis using an expanded genetic alphabet to quench fluorescence. Sherrill, C.B., Marshall, D.J., Moser, M.J., Larsen, C.A., Daudé-Snow, L., Jurczyk, S., Shapiro, G., Prudent, J.R. J. Am. Chem. Soc. (2004) [Pubmed]
First principles calculations of the pKa values and tautomers of isoguanine and xanthine. Rogstad, K.N., Jang, Y.H., Sowers, L.C., Goddard, W.A. Chem. Res. Toxicol. (2003) [Pubmed]
Synthesis, antiviral, and antitumor activity of 2-substituted purine methylenecyclopropane analogues of nucleosides. Qin, X., Chen, X., Wang, K., Polin, L., Kern, E.R., Drach, J.C., Gullen, E., Cheng, Y.C., Zemlicka, J. Bioorg. Med. Chem. (2006) [Pubmed]
The use of thymidine analogs to improve the replication of an extra DNA base pair: a synthetic biological system. Sismour, A.M., Benner, S.A. Nucleic Acids Res. (2005) [Pubmed]
2-Hydroxyadenine (isoguanine) as oxidative DNA damage: its formation and mutation inducibility. Kamiya, H., Kasai, H. Nucleic Acids Symp. Ser. (1995) [Pubmed]
Enzymatic recognition of the base pair between isocytidine and isoguanosine. Switzer, C.Y., Moroney, S.E., Benner, S.A. Biochemistry (1993) [Pubmed]
Parallel-stranded duplexes and quartet assemblies formed by oligonucleotides containing isoguanine. Seela, F., Wei, C., Melenewski, A., Leonard, P. Nucleic Acids Symp. Ser. (1997) [Pubmed]

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