29049-22-7

Usage

Uses

Used in Diagnostic Applications:
2'-deoxyxanthosine is used as a biomarker for the diagnosis of certain diseases, as it can indicate the presence or progression of specific conditions.
Used in Research and Biotechnology:
2'-deoxyxanthosine is used as a research tool for studying nucleic acids and their interactions, contributing to the understanding and advancement of genetics and molecular biology.
Used in Therapeutic Applications:
2'-deoxyxanthosine has potential therapeutic applications, as it may be utilized in the development of treatments for various diseases by targeting specific biological processes.

Upstream product

• 961-07-9 2'-Deoxyguanosine 
• 67616-35-7 2'-deoxyisoinosine 
• 194287-64-4 N₁-hydroxy-2'-deoxyinosine 
• 55514-92-6 N-nitrosoproline 
• 170871-02-0 5-amino-1-(3,5-di-O-tert-butyldimethylsilyl-2-deoxy-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 170871-05-3 5-(benzyloxycarbonyl)amino-1-(2-deoxy-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 37642-56-1 5-Amino-1-(2'-deoxy-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 170871-03-1 {3-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-carbamoyl-3H-imidazol-4-yl}-carbamic acid benzyl ester 

Relevant academic research and scientific papers

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.

Near ultraviolet radiation-mediated reaction between N-nitrosoproline and DNA: Isolation and identification of two new adducts, (R)- and (S)-8-(2-pyrrolidyl)-2′-deoxyguanosine

To explore possible genotoxicity of N-nitrosoproline (NPRO), we investigated near-ultraviolet radiation (UVA)-mediated chemical reaction of NPRO with 2′-deoxyguanosine (dG). An acidic solution containing NPRO and dG was irradiated with UVA and products we

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

A new synthesis of oxanosine and 2'-deoxyoxanosine

An easy and more efficient synthesis of oxanosine and 2'-deoxyoxanosine has been developed, a key step in the reported synthesis is a new photochemical transformation by UV irradiation of 1-hydroxy derivatives of inosine.

2'-Deoxyisoinosine: Synthesis of a highly fluorescent nucleoside and its incorporation into oligonucleotides

The synthesis of 2'-deoxyisoinosine (2a) and the related 2',3'- dideoxynucleosides 2b and 3 is reported. The 3'-phosphonate 4b as well as the phosphoramidite 4c were prepared and employed in solid-phase oligonucleotide synthesis.

Oligodeoxynucleotides embodying the ambiguous base Z, 5-amino-imidazole- 4-carboxamide

Short oligomers containing 5-amino-1-(2-deoxy-β-D- ribofuranosyl)imidazole -4-carboxamide (dZ) were synthesized in solution using the phosphotriester methodology. Usual acyl groups were used for the canonical bases. For the exocyclic amino function of Z residue, the hydrogenolyzable benzyloxycarbonyl group was introduced.

PREPARATION OF 2'-DEOXYXANTHOSINE BY NITROSATIVE DEAMINATION OF 2'-DEOXYGUANOSINE UNDER ALKALINE AQUEOUS CONDITIONS

2'-Deoxyxanthosine (dXao) has been prepared by treating 2'-deoxyguanosine (dGuo) wiyh basic nitroprusside.Succesful conversion appears to be favored by ionizing both dGuo (increasing its nucleophilicity) and dXao (protecting it from protolysis).