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:

98%,99%, ^*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:

• Description: 8-Oxo-2′-deoxyguanosine (88847-89-6) is a useful marker for DNA damage via a variety of oxidative processes.1?It is a critical biomarker for oxidative stress and carcinogenesis.2,3
• Uses: A marker compound indicative of DNA damage associated with mutagenesis and carcinogenesis. Can induce differentiation of Friend murine erythroleukemia cells in vitro. 8-Hydroxy-2′-deoxyguanosine has been used:as a standard to analyse the oxidative DNA damage in the placenta of normal and abnormal pregnancies by electrochemical detectionas a standard for high performance liquid chromatography (HPLC) with electrochemical detection (ECD) measurementas a standard for HPLC and as a urinary marker of oxidative stress in order to assess the potential?antioxidant?activity of green coffee bean extract (GCBE) in vivoas a standard for LC/MS/MS analysis

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:

methyl peroxide anion

4,5-dimethyl-2,3-dihydrofuran

orcinol

C₁₀H₁₂N₅O₄^(1-)

Refernces

• 1、 Grey, Carl,Adlercreutz, Patrick. "Time and concentration dependence of fenton-induced oxidation of dG". . p. 259 - 278. Retrieved 2006.
• 2、 Seto, Hiroshi,Koike, Hiroshi,Sasano, Hideo. "Hydroxylation of Deoxyguanosine at the C-8 Position in the Thiosulfate-Hydrogen Peroxide Reaction System. Evidence of Hydroxyl Radical Generation in the System". . p. 993 - 996. Retrieved 1994.
• 3、 Hofer, Tim,Moeller, Lennart. "Optimization of the workup procedure for the analysis of 8-oxo-7,8-dihydro-2′-deoxyguanosine with electrochemical detection". . p. 426 - 432. Retrieved 2002.
• 4、 Kobayashi, Teruyuki,Tsuchiya, Kazuyoshi,Nishida, Yuzo. "8-Hydroxy-2′-deoxyguanosine formation and DNA damage induced by a dinuclear manganese(IV) complex and hydrogen peroxide". . p. 2391 - 2392. Retrieved 1996.
• 5、 Martinez, Glaucia Regina,Ravanat, Jean-Luc,Cadet, Jean,De Medeiros, Marisa Helena Gennari,Di Mascio, Paolo. "Spiroiminodihydantoin nucleoside formation from 2′-deoxyguanosine oxidation by [18O-labeled] singlet molecular oxygen in aqueous solution". . p. 1326 - 1332. Retrieved 2007.
• 6、 Zheng, Yiying,Haratipour, Pouya,Kashemirov, Boris A.,McKenna, Charles E.. "Synthesis of 8-oxo-dGTP and its β,γ-CH2-, β,γ-CHF-, and β,γ-CF2- analogues". . . Retrieved 2021/02/22.
• 7、 Aoyama, Shuhei,Arimoto-Kobayashi, Sakae,Asahi, Chiharu,Hatano, Tsutomu,Kimura, Sachiko,Suzuki, Toshinori. "Isolation of new photoadducts from UVA-irradiated N-nitrosoproline with 2'-deoxyadenosine and characterization of photoadducts from DNA irradiated with N-nitrosoproline". . . Retrieved 2020/07/03.