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139307-94-1 | Guanosine 5'-(tetrahydrogen triphosphate), 2'-deoxy-7,8-dihydro-8-oxo-
CAS No: 139307-94-1 Catalog No: AG001AQ7 MDL No:
Product Description
Catalog Number:
AG001AQ7
Chemical Name:
Guanosine 5'-(tetrahydrogen triphosphate), 2'-deoxy-7,8-dihydro-8-oxo-
CAS Number:
139307-94-1
Molecular Formula:
C10H14N5O12P3
Molecular Weight:
489.1657
IUPAC Name:
[[(2R,3S,5R)-5-(2-amino-6,8-dioxo-1,7-dihydropurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
InChI:
InChI=1S/C10H16N5O14P3/c11-9-13-7-6(8(17)14-9)12-10(18)15(7)5-1-3(16)4(27-5)2-26-31(22,23)29-32(24,25)28-30(19,20)21/h3-5,16H,1-2H2,(H,12,18)(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,17)/t3-,4+,5+/m0/s1
InChI Key:
BUZOGVVQWCXXDP-VPENINKCSA-N
SMILES:
O=P(OP(=O)(OP(=O)O)O)OC[C@H]1O[C@H](C[C@@H]1O)N1C(=O)N=C2C1=NC(=NC2=O)N
Properties
Complexity:
1040
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
0
Exact Mass:
522.991g/mol
Formal Charge:
0
Heavy Atom Count:
32
Hydrogen Bond Acceptor Count:
15
Hydrogen Bond Donor Count:
8
Isotope Atom Count:
0
Molecular Weight:
523.18g/mol
Monoisotopic Mass:
522.991g/mol
Rotatable Bond Count:
8
Topological Polar Surface Area:
289A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-6.4
Literature
| Title | Journal |
|---|---|
| Oxidation of the guanine nucleotide pool underlies cell death by bactericidal antibiotics. | Science (New York, N.Y.) 20120420 |
| Reduction of 8-oxodGTP in the nucleotide pool by hMTH1 leads to reduction in mutations in the human lymphoblastoid cell line TK6 exposed to UVA. | Mutation research 20111001 |
| Mutagenicity of secondary oxidation products of 8-oxo-7,8-dihydro-2'-deoxyguanosine 5'-triphosphate (8-hydroxy-2'- deoxyguanosine 5'-triphosphate). | Mutation research 20110901 |
| Crystal structure of human MTH1 and the 8-oxo-dGMP product complex. | FEBS letters 20110819 |
| Effect of the Y955C mutation on mitochondrial DNA polymerase nucleotide incorporation efficiency and fidelity. | Biochemistry 20110726 |
| Cleavage of oxidized guanine nucleotide and ADP sugar by human NUDT5 protein. | Journal of biochemistry 20110601 |
| Caenorhabditis elegans NDX-4 is a MutT-type enzyme that contributes to genomic stability. | DNA repair 20110207 |
| Mutagenicity of oxidized DNA precursors in living cells: Roles of nucleotide pool sanitization and DNA repair enzymes, and translesion synthesis DNA polymerases. | Mutation research 20101128 |
| DNA polymerases involved in the incorporation of oxidized nucleotides into DNA: their efficiency and template base preference. | Mutation research 20101128 |
| Programmed cell death triggered by nucleotide pool damage and its prevention by MutT homolog-1 (MTH1) with oxidized purine nucleoside triphosphatase. | Mutation research 20101128 |
| Oxidized purine nucleotides, genome instability and neurodegeneration. | Mutation research 20101128 |
| Mycobacterial MazG is a novel NTP pyrophosphohydrolase involved in oxidative stress response. | The Journal of biological chemistry 20100903 |
| DNA repair and the origins of urinary oxidized 2'-deoxyribonucleosides. | Mutagenesis 20100901 |
| DNA repair in mammalian mitochondria: Much more than we thought? | Environmental and molecular mutagenesis 20100601 |
| Effects of base excision repair proteins on mutagenesis by 8-oxo-7,8-dihydroguanine (8-hydroxyguanine) paired with cytosine and adenine. | DNA repair 20100504 |
| CiMutT, an asidian MutT homologue, has a 7, 8-dihydro-8-oxo-dGTP pyrophosphohydrolase activity responsible for sanitization of oxidized nucleotides in Ciona intestinalis. | Genes & genetic systems 20100101 |
| Age-related alterations in the expression of MTH2 in the hippocampus of the SAMP8 mouse with learning and memory deterioration. | Journal of the neurological sciences 20091215 |
| Sources of extracellular, oxidatively-modified DNA lesions: implications for their measurement in urine. | Journal of clinical biochemistry and nutrition 20091101 |
| Proliferating cell nuclear antigen is protected from degradation by forming a complex with MutT Homolog2. | The Journal of biological chemistry 20090717 |
| Incorporation of 8-hydroxyguanosine (8-oxo-7,8-dihydroguanosine) 5'-triphosphate by bacterial and human RNA polymerases. | Free radical biology & medicine 20090615 |
| Global kinetic explorer: a new computer program for dynamic simulation and fitting of kinetic data. | Analytical biochemistry 20090401 |
| Roles of specialized DNA polymerases in mutagenesis by oxidized guanine. | Nucleic acids symposium series (2004) 20090101 |
| 8-oxo-7,8-dihydroguanosine triphosphate(8-oxoGTP) down-regulates respiratory burst of neutrophils by antagonizing GTP toward Rac, a small GTP binding protein. | Free radical research 20070601 |
| Efficient and erroneous incorporation of oxidized DNA precursors by human DNA polymerase eta. | Biochemistry 20070508 |
| Oxidative damage in nucleic acids and Parkinson's disease. | Journal of neuroscience research 20070401 |
| The GT to GC single nucleotide polymorphism at the beginning of an alternative exon 2C of human MTH1 gene confers an amino terminal extension that functions as a mitochondrial targeting signal. | Journal of molecular medicine (Berlin, Germany) 20060801 |
| MTH1, an oxidized purine nucleoside triphosphatase, prevents the cytotoxicity and neurotoxicity of oxidized purine nucleotides. | DNA repair 20060713 |
| Mutagenesis and carcinogenesis caused by the oxidation of nucleic acids. | Biological chemistry 20060401 |
| Synthesis and characterization of the oxidized dGTP lesions spiroiminodihydantoin-2'-deoxynucleoside-5'- triphosphate and guanidinohydantoin-2'-deoxynucleoside-5'- triphosphate. | The Journal of organic chemistry 20060303 |
| Transient state kinetic studies of the MutT-catalyzed nucleoside triphosphate pyrophosphohydrolase reaction. | Biochemistry 20051122 |
| Cloning and characterization of an Arabidopsis thaliana Nudix hydrolase homologous to the mammalian GFG protein. | Biochimica et biophysica acta 20050925 |
| Mutagenesis induced by oxidized DNA precursors: roles of Y family DNA polymerases in Escherichia coli. | Chemical research in toxicology 20050801 |
| Comprehensive analysis of cytosolic Nudix hydrolases in Arabidopsis thaliana. | The Journal of biological chemistry 20050701 |
| [MTH1, an oxidized purine nucleoside triphosphatase suppresses mitochondrial dysfunction and cell death caused by oxidative stress]. | Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20050701 |
| Multiple enzyme activities of Escherichia coli MutT protein for sanitization of DNA and RNA precursor pools. | Biochemistry 20050503 |
| Cellular 8-oxo-7,8-dihydro-2'-deoxyguanosine 5'-triphosphate pyrophosphohydrolase activity of human and mouse MTH1 proteins does not depend on the proliferation rate. | Free radical biology & medicine 20041115 |
| Crystallization and preliminary X-ray analysis of Escherichia coli MutT in binary and ternary complex forms. | Acta crystallographica. Section D, Biological crystallography 20040901 |
| Structure of human MTH1, a Nudix family hydrolase that selectively degrades oxidized purine nucleoside triphosphates. | The Journal of biological chemistry 20040806 |
| Analysis of spontaneous base substitutions generated in mutator strains of Bacillus subtilis. | FEMS microbiology letters 20040501 |
| An oxidized purine nucleoside triphosphatase, MTH1, suppresses cell death caused by oxidative stress. | The Journal of biological chemistry 20030926 |
| Mutations in putative mutator genes of Mycobacterium tuberculosis strains of the W-Beijing family. | Emerging infectious diseases 20030701 |
| Mouse MTH2 protein which prevents mutations caused by 8-oxoguanine nucleotides. | Biochemical and biophysical research communications 20030613 |
| A novel mechanism for preventing mutations caused by oxidation of guanine nucleotides. | EMBO reports 20030501 |
| Interactions of the products, 8-oxo-dGMP, dGMP, and pyrophosphate with the MutT nucleoside triphosphate pyrophosphohydrolase. | Biochemistry 20021231 |
| The mammalian mismatch repair pathway removes DNA 8-oxodGMP incorporated from the oxidized dNTP pool. | Current biology : CB 20020604 |
| Mutagenic target for hydroxyl radicals generated in Escherichia coli mutant deficient in Mn- and Fe- superoxide dismutases and Fur, a repressor for iron-uptake systems. | DNA repair 20020530 |
| Role of tryptophan residues in the recognition of mutagenic oxidized nucleotides by human antimutator MTH1 protein. | Journal of molecular biology 20020524 |
| Assessing the metabolic function of the MutT 8-oxodeoxyguanosine triphosphatase in Escherichia coli by nucleotide pool analysis. | The Journal of biological chemistry 20020503 |
| Deregulated DNA polymerase beta strengthens ionizing radiation-induced nucleotidic and chromosomal instabilities. | Oncogene 20020404 |
| A molecular basis for the selective recognition of 2-hydroxy-dATP and 8-oxo-dGTP by human MTH1. | The Journal of biological chemistry 20020308 |
| 8-oxo-dGTPase, which prevents oxidative stress-induced DNA damage, increases in the mitochondria from failing hearts. | Circulation 20011211 |
| Nitrogen dioxide as an oxidizing agent of 8-oxo-7,8-dihydro-2'-deoxyguanosine but not of 2'-deoxyguanosine. | Chemical research in toxicology 20010201 |
| Presence of potential nickel-responsive element(s) in the mouse MTH1 promoter. | Annals of clinical and laboratory science 20010101 |
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