Isoguanine

CAS: 3373-53-3

Ref. 3D-FI10401

Product Information

• Name: Isoguanine
• Synonyms: 2-Hydroxy-6-aminopurine, 2-Amino-6-hydroxy purine, 2-Hydroxyadenine, 2-Oxoadenine, 2-Oxyadenine, 2H-Purin-2-one, 6-amino-1,3-dihydro-, 2H-Purin-2-one, 6-amino-3,7-dihydro-, 6-Amino-2-hydroxypurine, 6-Amino-3,7-dihydro-2H-purin-2-one, 6-amino-1,7-dihydro-2H-purin-2-one, 6-amino-3,5-dihydro-2H-purin-2-one, Guanopterin, NSC 241501

Description

Isoguanine is a purine analog that inhibits the formation of dNTPs by glycosylating the hydroxyl group at the 3' position of the ribose sugar. Isoguanine has been shown to be an inhibitor of inflammatory diseases, such as arthritis, and has been used in clinical trials for cancer therapy. Isoguanine also inhibits the activity of DNA glycosylases, which are enzymes that remove sugar residues from DNA strands. Thermodynamic and kinetic data for reactions involving isoguanine have been determined using various spectroscopic methods. The reaction mechanism involves protonation of isoguanine followed by nucleophilic attack on the carbonyl carbon atom. The tautomerization pathway may be important in understanding the reactivity of isoguanine because it occurs more rapidly than protonation or nucleophilic attack.

Isoguanine can be synthesized by reacting aminopurines with formaldehyde in

• Brand: Biosynth

Chemical properties

• Molecular weight: 151.13 g/mol
• Formula: C₅H₅N₅O
• Purity: Min. 95%
• InChI: InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)
• InChI key: InChIKey=DRAVOWXCEBXPTN-UHFFFAOYSA-N
• SMILES: Nc1[nH]c(=O)nc2nc[nH]c12