Isoguanine

Isoguanineor2-hydroxyadenine is a purine base that is an isomerofguanine. 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.^[2]^[3]

Isoguanine
Names

Preferred IUPAC name 6-Amino-1,9-dihydro-2H-purin-2-one
Other names 2-Hydroxyadenine
Identifiers
CAS Number	3373-53-3^Y
3D model (JSmol)	Interactive image
ChemSpider	69351
ECHA InfoCard	100.020.144
EC Number	222-157-6
PubChem CID	76900
UNII	E335PK4428^Y
CompTox Dashboard (EPA)	DTXSID00187406
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
SMILES O=C1\N=C2\N=C/NC2=C(\N1)N
Properties
Chemical formula	C₅H₅N₅O
Molar mass	151.1261
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

It is used as a nucleobaseofhachimoji nucleic acids.^[4] In hachimoji DNA, it pairs with 1-methylcytosine, while in hachimoji RNA, it pairs with isocytosine.

Isoguanine-Isocytosine-base-pair

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): 1163–1171. Bibcode:1998BpJ....75.1163Y. doi:10.1016/S0006-3495(98)74035-4. PMC 1299791. PMID 9726918.

^ Andrzej Jaworski, Józef S. Kwiatkowski, Bogdan Lesyng: „Why isoguanine and isocytosine are not the components of the genetic code", International Journal of Quantum Chemistry, Supplement: Proceedings of the International Symposium on Quantum Biology and Quantum Pharmacology, 1985, 28 (Supplement S12), pp. 209–216 (doi:10.1002/qua.560280720).

^ Christopher Roberts, Rajanikanth Bandaru, Christopher Switzer: „Theoretical and Experimental Study of Isoguanine and Isocytosine: Base Pairing in an Expanded Genetic System", J. Am. Chem. Soc., 1997, 119 (20), pp. 4640–4649 (doi:10.1021/ja970123s).

^ Hoshika, Shuichi; et al. (22 February 2019). "Hachimoji DNA and RNA: A genetic system with eight building blocks". Science. 363 (6429): 884–887. Bibcode:2019Sci...363..884H. doi:10.1126/science.aat0971. PMC 6413494. PMID 30792304.

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

Last edited on 27 October 2022,

at 19:35

Languages

●This page was last edited on 27

October 2022, at 19:35 (UTC).

●Content is available under CC B

Y-SA 4.0 unless otherwise noted.