8-OXO-2'-DEOXYGUANOSINE

Base Information

• Chemical Name: 8-OXO-2'-DEOXYGUANOSINE
• CAS No.: 88847-89-6
• Molecular Formula: C10H13 N5 O5
• Molecular Weight: 283.244
• Hs Code.: 29349990
• Mol file: 88847-89-6.mol

Synonyms:7,8-Dihydro-8-oxo-2'-deoxyguanosine;7,8-Dihydro-8-oxodeoxyguanosine; 8-Hydroxy-2'-deoxyguanosine;8-Hydroxydeoxyguanosine; 8-Oxo-2'-deoxyguanosine;8-Oxo-7,8-dihydro-2'-deoxyguanosine; 8-Oxo-7,8-dihydrodeoxyguanosine; 8-Oxo-dG

Chemical Property of 8-OXO-2'-DEOXYGUANOSINE

Chemical Property:

• Appearance/Colour: White solid.
• Melting Point: 217-220°C
• PKA: 7.86±0.20(Predicted)
• PSA: 159.51000
• Density: 2.25 g/cm³
• LogP: -1.37070
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 10 mg/ml).

Purity/Quality:

97% ^*data from raw suppliers

8-Oxo-2’-deoxyguanosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: 8-OXO-2'-DEOXYGUANOSINE (also known as 8-hydroxy-2'-deoxyguanosine or oh8dG) is a well-established biomarker of oxidative DNA damage, implicated in processes such as carcinogenesis, mutagenesis, and toxicology. It is commonly quantified using analytical techniques like GC-MS, where isotopically labeled analogs, such as 8-[18O]hydroxy-2'-deoxyguanosine, serve as internal standards for accurate measurement. The compound arises from oxidative stress-induced modifications to guanine bases in DNA, reflecting cellular exposure to reactive oxygen species. Its detection is critical in assessing oxidative damage in biological samples, including DNA and urine.

Technology Process of 8-OXO-2'-DEOXYGUANOSINE

There total 51 articles about 8-OXO-2'-DEOXYGUANOSINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

8-(benzyloxy)-2'-deoxyguanosine (96964-90-8) → 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6)

Guidance literature:

With hydrogenchloride; In methanol; at 10 ℃; for 1h;

DOI:10.1016/S0960-894X(00)00310-3

Reference yield: 10.0%

2'-Deoxyguanosine (961-07-9) → 2,2-diamino-4-[(2-deoxy-β-D-erythro-pentofuranosyl)amino]-2,5-dihydrooxazol-5-one (137608-88-9) + 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6) + (4R*)-4,8-dihydro-4-hydroxy-8-oxo-2'-deoxyguanosine (137608-89-0) + (4S*)-4,8-dihydro-4-hydroxy-8-oxo-2'-deoxyguanosine (137608-90-3)

Guidance literature:

With methylene blue; In water; at 20 ℃; for 1h; Further byproducts given; UV-irradiation;

DOI:10.1021/tx00045a009

Reference yield: 6.6%

2'-Deoxyguanosine (961-07-9) → spiroiminodihydantoin-2'-deoxyribonucleoside + 5-carboxamido-5-formamido-2-iminohydantion-2′-deoxyribonucleoside + 5',8-cyclo-2'-deoxyguanosine + 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6) + N1-(β-D-erythro-pentofuranosyl)-5-guanidinohydantoin

Guidance literature:

With Fe(II)- EDTA; dihydrogen peroxide; oxygen; sodium L-ascorbate; In aq. phosphate buffer; at 22 ℃; for 1h; pH=7.4; Inert atmosphere;

DOI:10.1021/acs.joc.5b00689

upstream raw materials:

2'-Deoxyguanosine

8-(benzyloxy)-2'-deoxyguanosine

3,3-dimethyl-4-hydroxymethyl-4-phenyl-1,2-dioxetane

8-bromo-2'-deoxyguanosine

Downstream raw materials:

2,2-diamino-4-[(2-deoxy-β-D-erythro-pentofuranosyl)amino]-2,5-dihydrooxazol-5-one

4-hydroxy-8-oxo-4,8-dihydro-2'-deoxyguanosine

5-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-imino-2,3-dihydro-imidazol-4-one

C₁₇H₁₉N₅O₆

Refernces

Synthesis of 8-[¹⁸O]hydroxy-2'-deoxyguanosine

10.1002/jlcr.2580340213

The research aims to develop a method for synthesizing 8-[18O]hydroxy-2'-deoxyguanosine (8-[18O]OH-dG) to be used as an internal standard for the quantification of 8-hydroxy-2'-deoxyguanosine (oh8dG) by GC-MS. oh8dG is a significant marker of oxidatively damaged DNA, which is relevant in carcinogenesis, mutagenesis, and toxicology. The synthesis process involves several steps, starting with the bromination of 2'-deoxyguanosine to produce 8-bromo-2'-deoxyguanosine, followed by the conversion to 8-[18O]benzyloxy-2'-deoxyguanosine using the sodium salt of [18O]benzyl alcohol, and finally, the reduction to 8-[18O]hydroxy-2'-deoxyguanosine through catalytic transfer hydrogenation. Key chemicals used include 2'-deoxyguanosine, bromine, ethyl benzimidate hydrochloride, H218O, LiAlH4, sodium hydride, and palladium on carbon. The overall yield of 8-[18O]OH-dG from H218O was approximately 4%, with an isotopic purity of 93.4 atom% as determined by GC-MS. The synthesized compound meets the required purity standards for its intended application as an internal standard in the analysis of oh8dG extracted from in vivo DNA and urine.