Isoguanine

Isoguanine

IUPAC name 6-Amino-1,7-dihydropurin-2-one
Other names 2-Hydroxyadenine
Identifiers
CAS number	3373-53-3
PubChem	76900
ChemSpider	69351
Jmol-3D images	Image 1
SMILES O=C1\N=C2\N=C/NC2=C(\N1)N
InChI InChI=1/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11) Key: DRAVOWXCEBXPTN-UHFFFAOYAU
Properties
Molecular formula	C₅H₅N₅O
Molar mass	151.1261
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Isoguanine or 2-hydroxyladenine is a purine base that is an isomer of guanine. It is a product of oxidative damage to DNA and has been shown to cause mutation.^[1] It is also used in combination with isocytosine in studies of unnatural nucleic acid analogues of the normal base pairs in DNA.

References

^ Yang XL, Sugiyama H, Ikeda S, Saito I, Wang AH (1998). "Structural studies of a stable parallel-stranded DNA duplex incorporating isoguanine:cytosine and isocytosine:guanine basepairs by nuclear magnetic resonance spectroscopy". Biophys. J. 75 (3): 1163–71. doi:10.1016/S0006-3495(98)74035-4. PMC 1299791. PMID 9726918. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1299791.