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D5287

Sigma-Aldrich

2′-Deoxyinosine

≥98%

Synonyme(s) :

9-(2-Deoxy-β-D-ribofuranosyl)hypoxanthine

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About This Item

Formule empirique (notation de Hill):
C10H12N4O4
Numéro CAS:
890-38-0
Poids moléculaire :
252.23
Numéro Beilstein :
33517
Numéro CE :
212-964-1
Numéro MDL:
MFCD00005762
Code UNSPSC :
41106305
ID de substance PubChem :
24893935
Nomenclature NACRES :
NA.51

Source biologique

synthetic (organic)

Pureté

≥98%

Forme

powder

Impuretés

inosine, essentially free

Solubilité

1 M NH4OH: 50 mg/mL, clear, colorless

Température de stockage

−20°C

Chaîne SMILES 

OC[C@H]1O[C@H](C[C@@H]1O)n2cnc3C(=O)NC=Nc23

InChI

1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1

Clé InChI

VGONTNSXDCQUGY-RRKCRQDMSA-N

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Application

2′-Deoxyinosine has been used in the quantification of nucleoside forms of DNA lesion in a single DNA sample by liquid chromatography tandem mass spectrometry (LC-MS/MS). It has also been used as a standard for high performance liquid chromatography analysis.

Actions biochimiques/physiologiques

2′-Deoxyinosine is a nucleoside composed of hypoxanthine attached to 2′-deoxyribose via a β-N9-glycosidic bond. 2′-Deoxyinosine in DNA can arise from deamination of adenosine. 2′-deoxyinsine can be used as a model compound to study the chemistry of adduct formation and radical chemistry that may affect DNA structures. 2′-Deoxyinosine is used to produce hybridization-sensitive fluorescent DNA probes with self-avoidance ability.
2′-Deoxyinosine is a nucleoside form of hypoxanthine. It is a DNA damage product resulting from the impairment of DNA by reactive nitrogen species. 2′-deoxyinosine is formed from nitrosative deamination by N2O3.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

Shuji Ikeda et al.
Organic & biomolecular chemistry, 8(3), 546-551 (2010-01-22)
Hybridization-sensitive fluorescent probes have an inherent disadvantage: self-dimerization of the probe prevents the fluorescence quenching prior to hybridization with the target, resulting in a high background signal. To avoid self-dimerization of probes, we focused on a base pair formed by
Bo Pang et al.
Carcinogenesis, 28(8), 1807-1813 (2007-03-10)
In an effort to define the prevalent DNA damage chemistry-associated chronic inflammation, we have quantified 12 DNA damage products in tissues from the SJL mouse model of nitric oxide (NO) overproduction. Using liquid chromatography-mass spectrometry/MS and immunoblot techniques, we analyzed
Quantification of DNA damage products resulting from deamination, oxidation and reaction with products of lipid peroxidation by liquid chromatography isotope dilution tandem mass spectrometry
Taghizadeh K, et al.
Nature Protocols, 3(8), 1287-1287 (2008)
Bernard Weiss
DNA repair, 7(2), 205-212 (2007-11-06)
Deoxyinosine (dI) is produced in DNA by the hydrolytic or nitrosative deamination of deoxyadenosine. It is excised in a repair pathway that is initiated by endonuclease V, the product of the nfi gene. The repair was studied in vivo using
Manabu Yasui et al.
Journal of molecular biology, 377(4), 1015-1023 (2008-02-29)
Chronic inflammation involving constant generation of nitric oxide (*NO) by macrophages has been recognized as a factor related to carcinogenesis. At the site of inflammation, nitrosatively deaminated DNA adducts such as 2'-deoxyinosine (dI) and 2'-deoxyxanthosine are primarily formed by *NO
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