142559-87-3

Basic information

• Product Name: 5-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-imino-2,3-dihydro-imidazol-4-one
• Synonyms: 5-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-imino-2,3-dihydro-imidazol-4-one
• CAS NO: 142559-87-3
• Molecular Weight: 228.208
• Mol File: 142559-87-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-imino-2,3-dihydro-imidazol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-imino-2,3-dihydro-imidazol-4-one(142559-87-3)
• EPA Substance Registry System: 5-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2-imino-2,3-dihydro-imidazol-4-one(142559-87-3)

Safety Data

• Hazardous Substances Data: 142559-87-3(Hazardous Substances Data)

Upstream product

• 88847-89-6 7,8-dihydro-8-oxo-2'-deoxyguanosine 
• 961-07-9 2'-Deoxyguanosine 

Relevant articles and documents

Identification of the α and β anomers of 1-(2-deoxy-D-erythro- pentofuranosyl)-oxaluric acid at the site of riboflavin-mediated photooxidation of guanine in 2′-deoxyguanosine and thymidylyl-3′-5′- deoxyguanosine

Products of riboflavin-mediated photosensitization of 2′- deoxyguanosine (dG) and thymidylyl-(3′-5′)-2′-deoxyguanosine (TpdG) by 350-nm light in oxygen-saturated aqueous solution have been isolated and identified as 1-(2-deoxy-β-erythro-pentofuranosyl) oxaluric acid (β-dOx) and thymidylyl-(3′-5′)-1-(2-deoxy-β-D-erythro- pentofuranosyl) oxaluric acid (Tpβ-dOx), respectively. In aqueous solution the modified β-deoxyribonucleoside is slowly converted to the α-anomer, generating α-dOx and Tpα-dOx. These modified nucleosides and dinucleoside monophosphates have been isolated by HPLC and characterized by proton and carbon NMR spectroscopy, fast atom bombardment mass spectrometry, and enzymatic analyses. Both α-dOx and Tpα-dOx slowly convert back into the modified β-deoxyribonucleoside, indicating that the furanosidic anomers are in dynamic equilibrium. Relative to TpdG, the rate of hydrolysis of Tpβ-dOx and Tpα-dOx by spleen phosphodiesterase is greatly reduced. Hot piperidine (1.0 M, 90°C, 30 min) destroys Tpβ-dOx and Tpα-dOx. Riboflavin-mediated photosensitization of TpdG in D 2O instead of H2O has no detectable effect on the yield of Tpβ-dOx, suggesting that oxaluric acid is generated through a Type-I reaction mechanism, likely through the intermediary on initially generated 8-oxo-7,8-dihydro-2′-deoxyguanosine.

Photooxydation sensibilisee de la desoxy-2' guanosine par des phtalocyanines et naphtalocyanines. Determination de l'importance des mecanismes de type I et de type II

The photodynamic properties of sulfonated derivatives of phthalocyanine and naphthalocyanine were investigated using 2'-deoxyguanosine as a model compound for DNA.The major degradation photoproducts of this nucleoside were characterized and classified into two categories.The degradation involving the radical mechanism (type I) led to the formation of 2,2-diamino-5-oxazolone.The two main photooxidation products involving type II mechanism were characterized as the 4R* and 4S* diastereoisomers of 9-(2-β-D-deoxyerythropentofuranosyl)-4,8-dihydro-4-hydroxy-8-oxoguanine.In addition, 8-oxo-7,8-dihydro-2'-deoxyguanosine was shown to be generated (probably through type II mechanism).By identifying and quantifying these photoproducts, the ratio of type I/type II photoprocess was established for three (aluminum, gallium and zinc) disulfonated phthalocyanines and a tetrasulfonated aluminum naphthalocyanine.It was found that the type II mechanism is predominant.