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D7145

Sigma-Aldrich

2′-Deoxyguanosine monohydrate

99-100%

Synonym(s):

2′-Deoxyguanosine hydrate, 9-(2-Deoxy-β-D-ribofuranosyl)guanine, Guanine-2′-deoxyriboside

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O4 · H2O
CAS Number:
312693-72-4
Molecular Weight:
285.26
Beilstein:
39814
MDL number:
MFCD00150760
UNSPSC Code:
41106305
PubChem Substance ID:
24894083
NACRES:
NA.51

biological source

synthetic (organic)

Assay

99-100%

form

powder

solubility

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

InChI key

LZSCQUCOIRGCEJ-FPKZOZHISA-N

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Application

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 Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Zimu Deng et al.
Methods in molecular biology (Clifton, N.J.), 1323, 151-158 (2015-08-22)
Reconstituted thymus organ culture is based on fetal thymus organ culture (FTOC). Purified thymocyte populations, from genetically modified mice or even from other species, are cultured in vitro with thymic lobes depleted of their endogenous thymocytes (by 2'-deoxyguanosine treatment) to
Athanasios Valavanidis et al.
Free radical research, 39(10), 1071-1081 (2005-11-22)
An association between exposure to ambient particulate matter (PM) and increased incidence of mortality and morbidity due to lung cancer and cardiovascular diseases has been demonstrated by recent epidemiological studies. Reactive oxygen species (ROS), especially hydroxyl radicals, generated by PM
Aaron M Fleming et al.
Organic & biomolecular chemistry, 15(39), 8341-8353 (2017-09-25)
In DNA, 2'-deoxyguanosine (dG) is susceptible to oxidative modification by reactive oxygen species (ROS) yielding many products, one of which is 8-oxo-7,8-dihydro-2'-deoxyguanosine (dOG). Interestingly, dOG is stable but much more labile toward oxidation than dG, furnishing 5-guanidinohydantoin-2'-deoxyribose (dGh) that is
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