29049-22-7

Basic information

• Product Name: 2'-deoxyxanthosine
• Synonyms: 2'-deoxyxanthosine;Xanthosine, 2'-deoxy-;2'-dX;Xanthine 9-(beta-D-deoxyriboside);9-(2'-Deoxy-beta-D-ribosyl)xanthine;9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-2,6-dione
• CAS NO: 29049-22-7
• Molecular Formula: C₁₀H₁₂N₄O₅
• Molecular Weight: 268.2261
• Mol File: 29049-22-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 775.6°Cat760mmHg
• Flash Point: 422.9°C
• Appearance: /
• Density: 2.08g/cm³
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Water (Slightly, Sonicated)
• PKA: 7.33±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2'-deoxyxanthosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-deoxyxanthosine(29049-22-7)
• EPA Substance Registry System: 2'-deoxyxanthosine(29049-22-7)

Safety Data

• Hazardous Substances Data: 29049-22-7(Hazardous Substances Data)

Usage

General Description

2'-deoxyxanthosine is a modified nucleoside that is derived from the purine base xanthine. It is a key component of DNA and is involved in various biological processes, including the maintenance and replication of genetic information. 2'-deoxyxanthosine is a potential biomarker for the diagnosis of certain diseases and has been studied for its potential therapeutic applications. It is also used in research and biotechnology as a tool for studying nucleic acids and their interactions. Due to its importance in DNA, 2'-deoxyxanthosine plays a crucial role in understanding and advancing our knowledge of genetics and molecular biology.

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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.

Synthesis of 2',3'-didehydro-2',3'-dideoxyisoinosine and oxidation of fluorescent 2-hydroxypurine nucleosides by xanthine oxidase

The syntheses of 2',3'-didehydro-2',3'-dideoxyisoinosine (d4isoI, 4) as well as 7-deaza-2',3'-didehydro-2',3'-dideoxyisoinosine (d4c7isoI, 5) are described. Compounds 4 and 5 show both strong fluorescence. Compound 4 is oxidized by xanthine oxi