D5287

2′-Deoxyinosine

≥98%

• Synonym(s): 9-(2-Deoxy-β-D-ribofuranosyl)hypoxanthine
• Empirical Formula (Hill Notation): C₁₀H₁₂N₄O₄
• CAS Number: 890-38-0
• Molecular Weight: 252.23
• Beilstein: 33517
• EC Number: 212-964-1
• MDL number: MFCD00005762
• UNSPSC Code: 41106305
• PubChem Substance ID: 24893935
• NACRES: NA.51

Properties

• biological source: synthetic (organic)
• Assay: ≥98%
• form: powder
• impurities: inosine, essentially free
• solubility: 1 M NH₄OH: 50 mg/mL, clear, colorless
• storage temp.: −20°C
• SMILES string: 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
• InChI key: VGONTNSXDCQUGY-RRKCRQDMSA-N

Description

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.

Biochem/physiol Actions

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves