Guanosine

Title: Guanosine
CAS Registry Number: 118-00-3
Additional Names: 2-Amino-9-b-D-ribofuranosyl-9H-purine-6(1H)-one; guanine riboside; vernine
Molecular Formula: C10H13N5O5
Molecular Weight: 283.24
Percent Composition: C 42.40%, H 4.63%, N 24.73%, O 28.24%
Literature References: Constituent of nucleic acids. Prepn from yeast nucleic acid: P. A. Levene, L. W. Bass, Nucleic Acids (New York, 1931) p 163. Prepn from polynucleotides: P. A. Levene, E. Jorpes, J. Biol. Chem. 86, 389 (1930). Prepn from plants: H. Stendel, E. Peiser in G. Klein, Handbuch der Pflanzenanalyse IV (Vienna, 1933) p 448. Structure: Levene, Tipson, J. Biol. Chem. 97, 491 (1932); Gulland et al., J. Chem. Soc. 1934, 1639; Tsuboi et al., Biochim. Biophys. Acta 55, 1 (1962). Synthesis: Davoll, J. Chem. Soc. 1958, 1593. Tautomerism in aq soln: Miles et al., Science 142, 1458 (1963). Crystal structure and conformation: Bugg et al., Biochem. Biophys. Res. Commun. 3, 436 (1968). Review: Basic Principles in Nucleic Acid Chemistry vol. 1, P. O. P. Ts'o, Ed. (Academic Press, New York, 1974) passim.
Derivative Type: Dihydrate
Properties: Needles from water. Anhydr at 110°. Dec 240° in sealed tube (rapid heating). [a]D20 -61° (in water); [a]D24 -72° (c = 0.96 in 0.1N NaOH). uv max (pH 5.5): 188.3, 252.5 nm (e ´ 10-3 26.8, 13.7), Voet et al., Biopolymers 1, 193 (1963). One gram dissolves in 1320 ml water at 18°, in 33 ml boiling water. Soluble in dil mineral acids, in hot acetic acid, and in dil bases. Insol in alcohol, ether, chloroform, benzene.
Optical Rotation: [a]D20 -61° (in water); [a]D24 -72° (c = 0.96 in 0.1N NaOH)
Absorption maximum: uv max (pH 5.5): 188.3, 252.5 nm (e ´ 10-3 26.8, 13.7), Voet et al., Biopolymers 1, 193 (1963)
Guanoxabenz Guanoxan Guar Gum Guaran Guggulsterone

Guanosine
Guanosin.svg
Identifiers
CAS number 118-00-3 YesY
PubChem 765
ChemSpider 6544 YesY
UNII 12133JR80S YesY
DrugBank DB02857
KEGG C00387 YesY
MeSH Guanosine
ChEBI CHEBI:16750 YesY
ChEMBL CHEMBL375655 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H13N5O5
Molar mass 283.241
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Guanosine is a purine nucleoside comprising guanine attached to a ribose (ribofuranose) ring via a β-N9-glycosidic bond. Guanosine can be phosphorylated to become guanosine monophosphate (GMP), cyclic guanosine monophosphate (cGMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP). These forms play important roles in various biochemical processes such as synthesis of nucleic acids and proteins, photosynthesis, muscle contraction, and intracellular signal transduction (cGMP). When guanine is attached by its N9 nitrogen to the C1 carbon of a deoxyribose ring it is known as deoxyguanosine.

The antiviral drug aciclovir, often used in herpes treatment, is structurally similar to guanosine.

Guanosine is required for an RNA splicing reaction in mRNA, when a "self-splicing" intron removes itself from the mRNA message by cutting at both ends, re-ligating, and leaving just the exons on either side to be translated into protein.[1]

Guanosine with numbered carbons