Guanosine

Base Information

• Chemical Name: Guanosine
• CAS No.: 118-00-3
• Molecular Formula: C10H13N5O5
• Molecular Weight: 283.244
• Hs Code.: 29349990
• Mol file: 118-00-3.mol

Synonyms:Inosine, 2-amino-;2-amino-9-pentofuranosyl-9H-purin-6-ol;Ribofuranoside, guanine-9, .beta.-D-;Guanine, 9-.beta.-D-ribofuranosyl-;D-Guanosine;Guanosine(GR);2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one;Guo;Guanine-9-beta-D-ribofuranoside;2H-Purin-2-one,6-amino-1,3-dihydro-;beta-D-Ribofuranoside, guanine-9;2(3H)-Imino-9-.beta.-D-ribofuranosyl-9H-purin-6(1H)-one;9-beta-D-Ribofuranosylguanine;9H-purin-6-ol, 2-amino-9-pentofuranosyl-;9-(beta-D-Ribofuranosyl)guanine;2-Amino-9-.beta.-D-ribofuranosyl-9-H-purine-6(1H)-one;

Chemical Property of Guanosine

Chemical Property:

• Appearance/Colour: crystalline
• Vapor Pressure: 2.44E-25mmHg at 25°C
• Melting Point: 250 °C (dec.)(lit.)
• Refractive Index: -76 ° (C=1, 1mol/L NaOH)
• Boiling Point: 775.9°C at 760 mmHg
• PKA: pK1:1.9(＋1);pK2:9.25(0);pK3:12.33(OH) (25°C)
• Flash Point: 423.1oC
• PSA: 159.51000
• Density: 2.258 g/cm³
• LogP: -2.10550
• Storage Temp.: Store at RT.
• Solubility.: 0.1 M NaOH: 0.1 g/mL, clear, slightly yellow
• Water Solubility.: 0.75 g/L (25 ºC)

Purity/Quality:

98.5% ^*data from raw suppliers

Guanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 25
• Safety Statements: 45-24/25-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Guanosine is a purine nucleoside, in which the guanine attached to the C1 carbon of a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Its phosphorylated derivatives include GMP (guanosine monophosphate), cGMP (cyclic guanosine monophosphate), GDP (guanosine diphosphate), and GTP (guanosine triphosphate). These guanosine derivatives are very important in various biochemical processes, such as synthesis of nucleic acids and proteins, photosynthesis, muscle contraction, and intracellular signal transduction. Guanosine is thought to have neuroprotective properties. It can reduce neuroinflammation, oxidative stress, and excitotoxicity, as well as exerting trophic effects in neuronal and glial cells.?It is shown to be protective in central nervous system diseases including ischemic stroke, Alzheimer’s disease, Parkinson’s disease, spinal cord injury, nociception, and depression. Guanosine is found to be associated with purine nucleoside phosphorylase (PNP) deficiency, which is an inborn error of metabolism. Guanosine is a purine nucleoside that is comprised of the purine base guanine attached to a ribose moiety. Mono-, di-, tri-, and cyclic monophosphorylated forms of guanosine (GMP, GDP, GTP, and cGMP, respectively) are essential for a variety of endogenous biochemical processes, such as signal transduction, metabolism, and RNA synthesis.
• Uses: A constituent of nucleic acids. Guanosine has been used:as a reference standard for the analysis of glucosinolates by high-performance liquid chromatography with diode-array detection and electrospray ionization tandem mass spectrometry (HPLC-DAD-ESI/MS)as a component of Mouse Embryonic Fibroblasts (MEFs) cultureas a standard for the detection of residual RNA contaminant in oil palm plant genome samples by HPLC Guanosine is used as a constituent of nucleic acids. It is used in metallic paints, simulated pearls,plastics,cosmetics industry etc,. It has been also used in pharmacokinetics as a prodrug. Guanosine is used in cell culture applications as a precursor of GMP.

Technology Process of Guanosine

There total 161 articles about Guanosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[2-acetylamino-6-(2,4,6-triisopropyl-benzenesulfonyloxy)-purin-9-yl]-tetrahydro-furan-3-yl ester → 2?amino?9?(β?D?ribofuranosyl)purine (4546-54-7) + guanosine (118-00-3)

Guidance literature:

With palladium diacetate; triethylammonium formate; methylamine; Yield given. Multistep reaction. Yields of byproduct given; 1.) dioxane, 90 deg C;

DOI:10.1080/15257779408013268

Reference yield:

highly polymerized dsDNA from salmon testes → protoanemonin (108-28-1) + furfural (98-01-1) + Malondialdehyde (542-78-9) + N-oxycarbonylmethyl-5-methylene-Δ3-pyrrolin-2-one + G (118-00-3) + CYTIDINE (65-46-3) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) + adenosine (58-61-7)

Guidance literature:

With carbonatopentamminecobalt(III) nitrate hemihydrate; In aq. phosphate buffer; at 20 ℃; for 0.133333h; pH=6.9; UV-irradiation;

DOI:10.3109/10715762.2015.1081187

Reference yield:

3-(β-D-pentofuranosyl)pyrimido<1,2-a>purin-10(3H)-one (78880-62-3) → Malondialdehyde (542-78-9) + G (118-00-3)

Guidance literature:

With sodium hydroxide; water; at 45 ℃;

DOI:10.1246/cl.1981.707

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

(Ac)G(TMS)2

O^2'_,O3'_,O5'-tribenzoyl-guanosine

O⁶-(diphenylcarbamoyl)-N²-propionylguanosine

Downstream raw materials:

N¹-benzyl guanosine

8-benzylguanosine

N²-benzyl-2'-deoxyguanosine

2-Amino-7-benzyl-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-7-ium

Refernces

• 1、 Groziak, Michael P.,Chern, Ji-Wang,Townsend, Leroy B.. "Heterocyclic Synthesis via a 1,3-Dicyclohexylcarbodiimide-Mediated Cyclodesulfurative Annulation Reaction. New Methodology for the Preparation of Guanosine and Guanosine-Type Nucleoside Analogues". . p. 1065 - 1069. Retrieved 1986.
• 2、 Sallamand, Corinne,Miscioscia, Audrey,Lartia, Remy,Defrancq, Eric. "Phosphorylating reagent-free synthesis of 5′-phosphate oligonucleotides by controlled oxidative degradation of their 5′-end". . p. 2030 - 2033. Retrieved 2012.
• 3、 Gulland,Macrae. "-". . p. 662,666. Retrieved 1933.
• 4、 Hartmann,Bosshard. "-". . p. 1554,1560. Retrieved 1938.
• 5、 Vannoni,Giglioni,Santoro,Aceto,Marinello,Leoncini. "A kinetic study of the rat liver adenosine kinase reverse reaction". . p. 872 - 875. Retrieved 2008.
• 6、 Petruzzella, Emanuele,Curci, Alessandra,Margiotta, Nicola,Natile, Giovanni,Hoeschele, James D.. "Kiteplatin: Differential binding between GSH and GMP". . p. 130 - 136. Retrieved 2016.
• 7、 Ghidini, Alice,Ander, Charlotte,Winqvist, Anna,Stroemberg, Roger. "An RNA modification with remarkable resistance to RNase A". . p. 9036 - 9038. Retrieved 2013.
• 8、 Kawamura, Kunio. "Kinetic analysis of the cleavage of the ribose phosphodiester bond within guanine and cytosine-rich oligonucleotides and dinucleotides at 65-200 °C and its implications concerning the chemical evolution of RNA". . p. 153 - 162. Retrieved 2003.
• 9、 Chen, Fu,Davis, Jeffery T.,Gutierrez, Osvaldo,Lee, Wes,Xiao, Songjun,Zavalij, Peter Y.. "Oxidation of 8-thioguanosine gives redox-responsive hydrogels and reveals intermediates in a desulfurization pathway". . p. 6981 - 6984. Retrieved 2020.
• 10、 Serra, Immacolata,Ubiali, Daniela,Piskur, Jure,Christoffersen, Stig,Lewkowicz, Elizabeth S.,Iribarren, Adolfo M.,Albertini, Alessandra M.,Terreni, Marco. "Developing a collection of immobilized nucleoside phosphorylases for the preparation of nucleoside analogues: Enzymatic synthesis of arabinosyladenine and 2',3'-dideoxyinosine". . p. 157 - 165. Retrieved 2013.