88899-00-7

Basic information

• Product Name: 2'-deoxyoxanosine
• Synonyms: 2'-deoxyoxanosine
• CAS NO: 88899-00-7
• Molecular Formula: C₁₀H₁₂N₄O₅
• Molecular Weight: 268.23
• Mol File: 88899-00-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 707.2°C at 760 mmHg
• Flash Point: 381.5°C
• Appearance: /
• Density: 2.06g/cm³
• Vapor Pressure: 5.46E-21mmHg at 25°C
• Refractive Index: 1.854
• CAS DataBase Reference: 2'-deoxyoxanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-deoxyoxanosine(88899-00-7)
• EPA Substance Registry System: 2'-deoxyoxanosine(88899-00-7)

Safety Data

• Hazardous Substances Data: 88899-00-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12N4O5/c11-10-13-8-7(9(17)19-10)12-3-14(8)6-1-4(16)5(2-15)18-6/h3-6,15-16H,1-2H2,(H2,11,13)/t4-,5+,6-/m0/s1

Upstream product

• 961-07-9 2'-Deoxyguanosine 
• 55514-92-6 N-nitrosoproline 
• 194287-64-4 N₁-hydroxy-2'-deoxyinosine 

Relevant articles and documents

Isolation of new photoadducts from UVA-irradiated N-nitrosoproline with 2'-deoxyadenosine and characterization of photoadducts from DNA irradiated with N-nitrosoproline

N-nitrosoproline (NPRO) is formed from nitrosation of proline and has been reported to be non-carcinogenic and non-mutagenic. However, earlier studies in our laboratory showed that pre-irradiated NPRO can be converted to a mutagenic form. We previously investigated the reaction of NPRO with dA or dG under UVA irradiation and identified the formation of 2-pyrrolidyl-dA adducts (P1 & P2) and 8-pyrrolidyl-dG adducts (G1 & G2) as well as four known modified nucleosides, although several peaks found in the HPLC profiles of UVA-irradiated mixtures of dA and NPRO remain unidentified. In the present study we isolated new photoproducts from irradiated mixtures of dA and NPRO and identified (R)- and (S)-8-(2-pyrrolidyl)-2′-deoxyadenosine (A1 and A2) as products by MS and NMR. We also investigated the photoadducts formed in DNA treated with NPRO under UVA irradiation, and detected A1 and/or A2 (probably both), P1, P2, G1 and/or G2, and 8-oxodG as products. Under anaerobic conditions, formation of A1 and A2 was greater than that under aerobic conditions, suggesting that photo-reactions comprising pyrrolidyl radical with dA may increase under anaerobic conditions given reduced competition with oxidative photo-reactions which may decompose pyrrolidyl-dA adducts.

Formation of 2-chloroinosine from guanosine by treatment of HNO2 in the presence of NaCl

We investigated the reaction of Guo with nitrous acid in the presence of NaCl. When 1 mM Guo was incubated with 100 mM NaNO2 and 2 M NaCl in sodium acetate buffer at pH 3.2 and 37°C, 2-chloroinosine (2-Cl-Ino) was produced in addition to oxanosine (Oxo) and xanthosine (Xao). The yield of 2-Cl-Ino was 0.033 mM at an incubation time of 2 h. Under the same reaction conditions, GMP and dGuo gave rise to the corresponding 2-chloro derivatives with comparable yields. All the 2-chloro derivatives were fairly stable (t1/2>360 h) at physiological pH and temperature. To elucidate the reaction mechanism of the chlorination, the diazoate derivative of Guo, a reaction intermediate of the Guo-HNO2 system, was employed as a starting compound. When the diazoate was incubated with 2 M NaCl in a neutral solution, 2-Cl-Ino was produced in addition to Oxo and Xao. These results suggest that the 2-chloro derivatives can be produced from foodstuffs in the human stomach and may have potential importance as a carcinogen causing gastric cancer.

Isolation and characterization of a novel product, 2′-deoxyoxanosine, from 2′-deoxyguanosine, oligodeoxynucleotide, and calf thymus DNA treated by nitrous acid and nitric oxide

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