2133-80-4

Basic information

• Product Name: Azaguanosine
• Synonyms: Azaguanosine;5-Amino-3,4-dihydro-3-(β-D-ribofuranosyl)-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one;5-Amino-3,6-dihydro-3-β-D-ribofuranosyl-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one;5-Amino-3,6-dihydro-3-β-D-ribofuranosyl-7H-v-triazolo[4,5-d]pyrimidin-7-one;8-Azaguanosine
• CAS NO: 2133-80-4
• Molecular Formula: C9H12 N6 O5
• Molecular Weight: 284.23
• Mol File: 2133-80-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 250-252 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 567.3°C at 760 mmHg
• Flash Point: 296.9°C
• Appearance: /
• Density: 2.49g/cm³
• Vapor Pressure: 3.13E-15mmHg at 25°C
• Refractive Index: 2.059
• PKA: 8.32±0.20(Predicted)
• CAS DataBase Reference: Azaguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: Azaguanosine(2133-80-4)
• EPA Substance Registry System: Azaguanosine(2133-80-4)

Safety Data

• Hazardous Substances Data: 2133-80-4(Hazardous Substances Data)

Usage

Uses

8-Azaguanosine is an azapurine nucleoside.An extensive study has been made of the fluorescence emission properties of the neutral and ionic forms in aqueous medium of the 8-Azaguanosine. The 8-?azaguanosine is a substrate of purine nucleoside phosphorylase (PNP)?.

InChI:InChI=1/C9H12N6O5/c10-9-11-6-3(7(19)12-9)13-14-15(6)8-5(18)4(17)2(1-16)20-8/h2,4-5,8,14,16-18H,1H2,(H2,10,12,19)/t2-,4-,5-,8-/m1/s1

Upstream product

• 38874-35-0 [(2R,3R,4R,5R)-5-(5-amino-7-oxo-6H-triazolo[4,5-d]pyrimidin-3-yl)-3,4-dibenzoyloxy-tetrahydrofuran-2-yl]methyl benzoate 
• 134-58-7 8-azaguanine 
• 18646-11-2 α-D-ribofuranosyl-1-phosphate 
• 58-96-8 uridine 
• 86480-36-6 3-β-D-ribofuranosyl-5-(methylthio)-3H-1,2,3-triazolo<4,5-d>pyrimidin-7-amine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 18646-11-2 ribofuranose-1-phosphate 
• 122147-05-1 2-methylsulfanyl-8-aza-inosine 

Downstream Products

• 4730-45-4 8-Aza-xanthosin 

Relevant articles and documents

Enzymatic synthesis of highly fluorescent 8-azapurine ribosides using a purine nucleoside phosphorylase reverse reaction: Variable ribosylation sites

Various forms of purine-nucleoside phosphorylase (PNP) were used as catalysts of enzymatic ribosylation of selected fluorescent 8-azapurines. It was found that the recombinant calf PNP catalyzes ribosylation of 2,6-diamino-8-azapurine in a phosphate-free medium, with ribose-1-phosphate as ribose donor, but the ribosylation site is predominantly N7 and N8, with the proportion of N8/N7 ribosylated products markedly dependent on the reaction conditions. Both products are fluorescent. Application of the E. coli PNP gave a mixture of N8 and N9-substituted ribosides. Fluorescence of the ribosylated 2,6-diamino-8-azapurine has been briefly characterized. The highest quantum yield, ~0.9, was obtained for N9-β-D-riboside (λmax 365 nm), while for N8-β-D-riboside, emitting at ~430 nm, the fluorescence quantum yield was found to be close to 0.4. Ribosylation of 8-azaguanine with calf PNP as a catalyst goes exclusively to N9. By contrast, the E. coli PNP ribosylates 8-azaGua predominantly at N9, with minor, but highly fluorescent products ribosylated at N8/N7.

Aeromonas hydrophila strains as biocatalysts for transglycosylation

Microbial transglycosylation is useful as a green alternative in the preparation of purine nucleosides and analogues, especially for those that display pharmacological activities. In a search for new transglycosylation biocatalysts, two Aeromonas hydrophila strains were selected. The substrate specificity of both micro-organisms was studied and, as a result, several nucleoside analogues have been prepared. Among them, ribavirin, a broad spectrum antiviral, and the well-known anti HIV didanosine, were prepared, in 77 and 62% yield using A. hydrophila CECT 4226 and A. hydrophila CECT 4221, respectively. In order to scale-up the processes, the reaction conditions, product purification and biocatalyst preparation were analyzed and optimized.

Spectroscopic and kinetic studies of interactions of calf spleen purine nucleoside phosphorylase with 8-azaguanine, and its 9-(2-phosphonylmethoxyethyl) derivative

Spectroscopic and kinetic studies of interactions of calf spleen purine nucleoside phosphorylase with 8-azaguanine, an excellent fluorescent/fluorogenic substrate for the synthetic pathway of the reaction, and its 9-(2-phosphonylmethoxyethyl) derivative, a bisubstrate analogue inhibitor, were carried out. The goal was to clarify the catalytic mechanism of the enzymatic reaction by identification of ionic/tautomeric forms of these ligands in the complex with PNP. Copyright Taylor & Francis, Inc.