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Isoguanine

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]

Isoguanine
Names
Preferred IUPAC name
6-Amino-1,9-dihydro-2H-purin-2-one
Other names
2-Hydroxyadenine
Identifiers
  • 3373-53-3 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 69351
ECHA InfoCard 100.020.144
EC Number
  • 222-157-6
  • 76900
UNII
  • E335PK4428 Y
  • DTXSID00187406
  • 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
  • O=C1\N=C2\N=C/NC2=C(\N1)N
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).

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.

Isoguanine-Isocytosine-base-pair

References Edit

  1. ^ 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.
  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).
  4. ^ 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.


isoguanine, hydroxyadenine, purine, base, that, isomer, guanine, product, oxidative, damage, been, shown, cause, mutation, also, used, combination, with, isocytosine, studies, unnatural, nucleic, acid, analogues, normal, base, pairs, namespreferred, iupac, nam. 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 Isoguanine NamesPreferred IUPAC name 6 Amino 1 9 dihydro 2H purin 2 oneOther names 2 HydroxyadenineIdentifiersCAS Number 3373 53 3 Y3D model JSmol Interactive imageChemSpider 69351ECHA InfoCard 100 020 144EC Number 222 157 6PubChem CID 76900UNII E335PK4428 YCompTox Dashboard EPA DTXSID00187406InChI 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 UHFFFAOYAUSMILES O C1 N C2 N C NC2 C N1 NPropertiesChemical formula C5H5N5OMolar mass 151 1261Except 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 nucleobase of hachimoji nucleic acids 4 In hachimoji DNA it pairs with 1 methylcytosine while in hachimoji RNA it pairs with isocytosine Isoguanine Isocytosine base pairReferences Edit 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 Jozef 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 nbsp This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Isoguanine amp oldid 1118576021, wikipedia, wiki, book, books, library,

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