Isoguanine

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Structural formula
Structural formula of isoguanine
General
Surname Isoguanine
other names
  • 6-amino-1,9-dihydropurin-2-one
  • 6-amino-2-oxo-purine
Molecular formula C 5 H 5 N 5 O
External identifiers / databases
CAS number 3373-53-3
EC number 222-157-6
ECHA InfoCard 100.020.144
PubChem 76900
ChemSpider 69351
Wikidata Q6085780
properties
Molar mass 151.13 g mol −1
Physical state

firmly

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isoguanine is a heterocyclic organic compound with a purine backbone. It is an isomer of the nucleobase guanine , with the amino group and carbonyl group switching places. Among other things, it is part of the nucleoside isoguanosine .

use

Isoguanine is used together with isocytosine to investigate unusual base pairings in DNA .

Isoguanine-isocytosine base pairing

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  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. ↑ Xiang-Lei Yang, Hiroshi Sugiyama, Shuji Ikeda, Isao Saito, Andrew H.-J. Wang: "Structural Studies of a Stable Parallel-Stranded DNA Duplex Incorporating Isoguanine: Cytosine and Isocytosine: Guanine Basepairs by Nuclear Magnetic Resonance Spectroscopy," Biophys. J. , 1998 , 75  (3), pp. 1163-1171 ( PMID 9726918 ; PMC 1299791 (free full text); doi : 10.1016 / S0006-3495 (98) 74035-4 ).

Web links

  • Entry for Isoguanine in the Human Metabolome Database (HMDB) , accessed October 30, 2013.