Chemistry:Isoguanine
From HandWiki
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| Preferred IUPAC name
6-Amino-1,9-dihydro-2H-purin-2-one | |
| Other names
2-Hydroxyadenine
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3D model (JSmol)
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| Properties | |
| 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 | |
Tracking categories (test):
Isoguanine or 2-hydroxyadenine 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.[2][3]
It is used as a nucleobase of hachimoji nucleic acids.[4] In hachimoji DNA, it pairs with 1-methylcytosine, while in hachimoji RNA, it pairs with isocytosine.
References
- ↑ "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. 1998. doi:10.1016/S0006-3495(98)74035-4. PMID 9726918. Bibcode: 1998BpJ....75.1163Y.
- ↑ 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 (22 February 2019). "Hachimoji DNA and RNA: A genetic system with eight building blocks". Science 363 (6429): 884–887. doi:10.1126/science.aat0971. PMID 30792304. Bibcode: 2019Sci...363..884H.
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