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Merck

D7145

Sigma-Aldrich

2′-Desoxyguanosin Monohydrat

99-100%

Synonym(e):

9-(2-Deoxy-β-D-ribofuranosyl)-guanin, Guanindeoxyribosid

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About This Item

Empirische Formel (Hill-System):
C10H13N5O4 · H2O
CAS-Nummer:
Molekulargewicht:
285.26
Beilstein:
39814
MDL-Nummer:
UNSPSC-Code:
41106305
PubChem Substanz-ID:
NACRES:
NA.51

Biologische Quelle

synthetic (organic)

Assay

99-100%

Form

powder

Löslichkeit

1 M NH4OH: 50 mg/mL, clear, colorless

SMILES String

O.NC1=Nc2c(ncn2[C@H]3C[C@H](O)[C@@H](CO)O3)C(=O)N1

InChI

1S/C10H13N5O4.H2O/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6;/h3-6,16-17H,1-2H2,(H3,11,13,14,18);1H2/t4-,5+,6+;/m0./s1

InChIKey

LZSCQUCOIRGCEJ-FPKZOZHISA-N

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Anwendung

2′-Deoxyguanosine monohydrate has been used as a nucleoside supplement:
  • to study its effect on mitochondrial DNA copy number in deoxyguanosine kinase (dguok) mutant zebrafish,
  • in tissue culture medium for deoxyribonucleotide triphosphate (dNTP) synthesis,
  • in RPMI (Roswell Park Memorial Institute)-1640 medium to eliminate the endogenous thymocytes

Biochem./physiol. Wirkung

Deoxyguanosine (dG) is a purine nucleoside that upon sequential phosphorylation (kinases) forms deoxyguanosine triphosphate (dGTP) which is used by DNA polymerases and reverse transcriptases to synthesize DNA(s). Deoxyguanosine is the most electron-rich of the four canonical bases and includes many nucleophilic sites which are susceptible to oxidative damage. This makes deoxyguanosine and its oxidized derivatives useful reagents to study mechanisms of oxidative damage to nucleosides and nucleotides.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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José Pedro F Angeli et al.
Free radical biology & medicine, 51(2), 503-515 (2011-05-24)
Epidemiological studies have indicated that Western diets are related to an increase in a series of malignancies. Among the compounds that are credited for this toxic effect are heme and lipid peroxides. We evaluated the effects of hemoglobin (Hb) and
Sreelekha K Singh et al.
Nucleic acids research, 39(15), 6789-6801 (2011-05-17)
The oxidation of DNA resulting from reactive oxygen species generated during aerobic respiration is a major cause of genetic damage that, if not repaired, can lead to mutations and potentially an increase in the incidence of cancer and aging. A
Kasper Broedbaek et al.
Free radical biology & medicine, 51(8), 1473-1479 (2011-08-09)
The increasing prevalence of diabetes together with the associated morbidity and mortality calls for additional preventive and therapeutic strategies. New biomarkers that can be used in therapy control and risk stratification as alternatives to current methods are needed and can
Takeji Takamura-Enya et al.
Bioorganic & medicinal chemistry letters, 21(14), 4206-4209 (2011-06-21)
BODIPY-modified 2'-deoxyguanosine was synthesized for use as a detection reagent for genotoxic compounds. BODIPY-FL is a well known fluorescence reagent whose fluorescent light emission diminishes near a guanine base by a photo-induced electron transfer process. We attached BODIPY-Fl to the
Benjamin Munro et al.
Human molecular genetics, 28(5), 796-803 (2018-11-15)
Deoxyguanosine kinase (dGK) is an essential rate-limiting component of the mitochondrial purine nucleotide salvage pathway, encoded by the nuclear gene encoding deoxyguanosine kinase (DGUOK). Mutations in DGUOK lead to mitochondrial DNA (mtDNA) depletion typically in the liver and brain, causing

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