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Isoguanine

CAS No.:
3373-53-3
Catalog Number:
AG0034BL
Molecular Formula:
C5H5N5O
Molecular Weight:
151.1261
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
250mg
95%
In Stock USA
United States
$150
- +
1g
95%
In Stock USA
United States
$438
- +
5g
95%
In Stock USA
United States
$1750
- +
Product Description
Catalog Number:
AG0034BL
Chemical Name:
Isoguanine
CAS Number:
3373-53-3
Molecular Formula:
C5H5N5O
Molecular Weight:
151.1261
MDL Number:
MFCD00142931
IUPAC Name:
6-amino-1,7-dihydropurin-2-one
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:
DRAVOWXCEBXPTN-UHFFFAOYSA-N
SMILES:
O=c1nc(N)c2c([nH]1)nc[nH]2
EC Number:
222-157-6
UNII:
E335PK4428
NSC Number:
241501
Properties
Complexity:
313  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
151.049g/mol
Formal Charge:
0
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
151.129g/mol
Monoisotopic Mass:
151.049g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
91.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.7  
Literature
Title Journal
Solution structure of a parallel-stranded oligoisoguanine DNA pentaplex formed by d(T(iG)4 T) in the presence of Cs+ ions. Angewandte Chemie (International ed. in English) 20120806
Isoguanine formation from adenine. Chemistry (Weinheim an der Bergstrasse, Germany) 20120416
Rescue of the orphan enzyme isoguanine deaminase. Biochemistry 20110628
Preparation of the 2'-deoxynucleosides of 2,6-diaminopurine and isoguanine by direct glycosylation. The Journal of organic chemistry 20100305
Examination of the effect of the annealing cation on higher order structures containing guanine or isoguanine repeats. Chemistry (Weinheim an der Bergstrasse, Germany) 20091026
An ab initio study of substituent effects on the excited states of purine derivatives. The journal of physical chemistry. A 20081204
An alternative nucleobase code: characterization of purine-purine DNA double helices bearing guanine-isoguanine and diaminopurine 7-deaza-xanthine base pairs. Chembiochem : a European journal of chemical biology 20081124
Stacking effects on local structure in RNA: changes in the structure of tandem GA pairs when flanking GC pairs are replaced by isoG-isoC pairs. The journal of physical chemistry. B 20070621
RNA polymerase II bypasses 8-oxoguanine in the presence of transcription elongation factor TFIIS. DNA repair 20070601
An unusual mode of DNA duplex association: Watson-Crick interaction of all-purine deoxyribonucleic acids. Chemistry & biology 20070501
Replication of 2-hydroxyadenine-containing DNA and recognition by human MutSalpha. DNA repair 20070301
Density functional study of isoguanine tetrad and pentad sandwich complexes with alkali metal ions. Journal of molecular modeling 20070201
Oligonucleotide transformation for the study of mutagenic specificities of DNA lesions in yeast. Nucleic acids symposium series (2004) 20070101
pH-Independent triplex formation: hairpin DNA containing isoguanine or 9-deaza-9-propynylguanine in place of protonated cytosine. Organic & biomolecular chemistry 20061107
Mutagenesis and carcinogenesis caused by the oxidation of nucleic acids. Biological chemistry 20060401
[Defense mechanisms against oxidative damage in mitochondrial genome]. Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20051101
A potential prebiotic route to adenine from hypoxanthine. Chemistry & biodiversity 20050701
Parallel DNA double helices incorporating isoG or m5isoC bases studied by FTIR, CD and molecular modeling. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20050201
Gold DNA-conjugates: ion specific self-assembly of gold nanoparticles via the dG-quartet. Nucleosides, nucleotides & nucleic acids 20050101
Nucleic acid analysis using an expanded genetic alphabet to quench fluorescence. Journal of the American Chemical Society 20040414
Mutagenicities of 8-hydroxyguanine and 2-hydroxyadenine produced by reactive oxygen species. Biological & pharmaceutical bulletin 20040401
5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination. Journal of the American Chemical Society 20040303
Unique tautomeric properties of isoguanine. Journal of the American Chemical Society 20040114
First principles calculations of the pKa values and tautomers of isoguanine and xanthine. Chemical research in toxicology 20031101
Neighbouring bases in template influence base-pairing of isoguanine. The Biochemical journal 20030201
[Parallel-stranded DNA with natural base sequences]. Molekuliarnaia biologiia 20030101
Probing structure and function with alternative nucleic acids bearing 2',5'-linked, zwitterionic, and isocytosine-isoguanine components. Methods (San Diego, Calif.) 20010201
Regulation of intracellular localization of human MTH1, OGG1, and MYH proteins for repair of oxidative DNA damage. Progress in nucleic acid research and molecular biology 20010101
Parallel DNA containing pyrazolo[3,4-D]pyrimidine analogues of isoguanine. Nucleosides, nucleotides & nucleic acids 20010101
[Specific interactions of isoguanine with the neutral and deprotonated carboxylic group of amino acids: results of model quantum chemical calculations]. Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20010101
Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii. Biochemical pharmacology 19951109
Formation of 2-hydroxydeoxyadenosine triphosphate, an oxidatively damaged nucleotide, and its incorporation by DNA polymerases. Steady-state kinetics of the incorporation. The Journal of biological chemistry 19950818
Properties