Guanosine

Guanosine Basic information
Description Reference
Product Name:Guanosine
Synonyms:usafcb-11;O-(BETA-D-RIBOFURANOSYL)GUANINE;D-GUANOSINE;GR;GUANOSINE;GUANINE-9-BETA-D-RIBOFURANOSIDE;GUANINE RIBOSIDE;9-[BETA-D-RIBOFURANOSYL]GUANINE
CAS:118-00-3
MF:C10H13N5O5
MW:283.24
EINECS:204-227-8
Product Categories:Inhibitors;nucleoside;Nucleic acids;Bases & Related Reagents;Nucleotides;Carbohydrates & Derivatives;Pharmaceutical Intermediates;Purine;API intermediates;Nucleotides and Nucleosides;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;118-00-3
Mol File:118-00-3.mol
Guanosine Structure
Guanosine Chemical Properties
Melting point 250 °C (dec.) (lit.)
alpha -62 º (c=3, in 0.1 N NaOH)
Boiling point 425.8°C (rough estimate)
density 1.3790 (rough estimate)
refractive index -76 ° (C=1, 1mol/L NaOH)
storage temp. room temp
solubility 0.1 M NaOH: 0.1 g/mL, clear, slightly yellow
pkapK1:1.9(+1);pK2:9.25(0);pK3:12.33(OH) (25°C)
form Powder
color White to light yellow
OdorOdorless
optical activity[α]20/D -73±2°, c = 1.5% in 1 M NaOH
Water Solubility 0.75 g/L (25 ºC)
Merck 14,4566
BRN 625911
InChIKeyNYHBQMYGNKIUIF-UUOKFMHZSA-N
LogP-2.331 (est)
CAS DataBase Reference118-00-3(CAS DataBase Reference)
NIST Chemistry Referenceguanosine(118-00-3)
EPA Substance Registry SystemGuanosine (118-00-3)
Safety Information
Hazard Codes T,Xi
Risk Statements 25
Safety Statements 45-24/25-23
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS MF8750000
10-23
Hazard Note Irritant
TSCA Yes
HazardClass 6.1
PackingGroup 
HS Code 29349990
MSDS Information
ProviderLanguage
2-Amino-9-beta-D-ribofuranosyl-9H-purine-6-(1H)-one hydrate English
SigmaAldrich English
ACROS English
ALFA English
Guanosine Usage And Synthesis
DescriptionGuanosine 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.
ReferenceL. E. B. Bettio, J. Gil-Mohapel, A. L. S. Rodrigues, Guanosine and its role in neurophathologies, Purinergic Signal, 2016, vol. 12, pp. 411-426
DescriptionGuanosine 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.
Chemical PropertiesWhite, crystalline powder; odorless; mild saline taste. Very slightly soluble in cold water; soluble in boiling water, dilute mineral acids, hot acetic acid, and dilute bases; insoluble in alcohol, ether, chloroform, and benzene.
UsesGuanosine 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.
UsesGuanosine 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) culture
  • as a standard for the detection of residual RNA contaminant in oil palm plant genome samples by HPLC

DefinitionA NUCLEOSIDE present in DNA and RNA and consisting of guanine linked to D-ribose via a β-glycosidic bond.
DefinitionChEBI: A purine nucleoside in which guanine is attached to ribofuranose via a beta-N9-glycosidic bond.
General DescriptionGuanosine is an aromatic organic molecule and a purine nucleoside. It is present in the cerebrospinal fluid, intestinal cells, blood-brain barrier and in brain microvessels.
Biochem/physiol ActionsGuanosine nucleoside elicits cellular effect as the guanine-based purinergic system. It modulates glutamate uptake by glutamate transporters. It may have neuroprotective functionality in central nervous system disorders. Guanosine promotes neurite arborization, outgrowth, proliferation and differentiation. Administration of guanosine replenished GTP and elicits protective function in renal ischemic injury.
Purification MethodsIt crystallises from water as a dihydrate. Dry it at 110o.[Beilstein 26/18 V 81.]
Guanosine Preparation Products And Raw materials
Preparation ProductsAcyclovir-->Ribavirin-->Guanosine 5'-monophosphate disodium salt-->Calcium 5'-ribonucleotide-->5'-Guanylic acid-->7-METHYLGUANINE-->N,9-Diacetylguanine-->guanosine 3'-(dihydrogen phosphate)-->2',3'-cyclic UMP-->5-Bromouridine-->7,8-Dihydro-7-methylguanosine-->5-Methyluridine-->cytidine 2',3'-(hydrogen phosphate)-->7-METHYLGUANOSINE-->8-HYDROXYGUANOSINE-->6-THIOGUANOSINE
2'-O-MB-CGMP SODIUM SALT 8-AMINOGUANOSINE N2-Benzoyl-D-guanosine Guanylyl Imidodiphosphate N2-METHYLGUANOSINE GUANOSINE 5'-DIPHOSPHATE TRIS SALT 2'-Deoxyguanosine-5'-diphosphate trisodium salt TIMTEC-BB SBB006472 GTP TRIS SALT GUANOSINE-3',5'-CYCLIC-MONOPHOSPHORIC ACID SODIUM SALT,GUANOSINE 3',5'-MONOPHOSPHATE MONOSODIUM SALT,GUANOSINE 3',5'-CYCLOPHOSPHATE MONOSODIUM SALT 1-METHYLGUANOSINE 5'-Guanylic acid 2-AMINO-8-BROMO-9-((2R,3R,4S,5R)-3,4-DIHYDROXY-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-2-YL)-1,9-DIHYDRO-PURIN-6-ONE L-GUANOSINE, [8-3H]- N2,2'-O-DIBUTYRYLGUANOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT 8-BR-CGMP 8-MERCAPTOGUANOSINE 2',3',5'-Triacetylguanosine

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