イソグアニン

イソグアニン
	優先IUPAC名 6-Amino-1,9-dihydro-2H-purin-2-one
	別称 2-Hydroxyadenine
識別情報
CAS登録番号	3373-53-3
PubChem	76900
ChemSpider	69351
UNII	E335PK4428
EC番号	222-157-6
	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;
特性
化学式	C5H5N5O
モル質量	151.1261 g/mol
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

イソグアニン（英語: isoguanine）または、2-ヒドロキシアデニン（英語: 2-hydroxyadenine）は、プリン塩基の1つで、グアニンの異性体。DNAの酸化的損傷の産物であり、突然変異を引き起こすことが示されている^[1]。また、DNAの正常塩基対の非天然核酸アナログ（英語版）の研究では、イソシトシンと組み合わせて使用される^[2]^[3]。

ハチモジ核酸の核酸塩基として使用される^[4]。ハチモジDNAでは、1-メチルシトシンと対になり、ハチモジRNAではイソシトシンと対になる。

出典

^ “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). 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 (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.

[1] “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). Bibcode: 1998BpJ....75.1163Y. doi:10.1016/S0006-3495(98)74035-4. PMC 1299791. PMID 9726918.

[2] 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).

[3] 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).

[SCI-20190222-4] Hoshika, Shuichi (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.

[1]

[2]

[3]

[4]