Guanosine

Names
IUPAC name Guanosine[1]
Systematic IUPAC name 2-Amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,9-dihydro-6H-purin-6-one
Other names Guanine riboside
Identifiers
CAS Number	118-00-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16750 Y
ChEMBL	ChEMBL375655 Y
ChemSpider	6544 Y
DrugBank	DB02857 Y
ECHA InfoCard	100.003.844
IUPHAR/BPS	4567
KEGG	C00387 Y
MeSH	Guanosine
PubChem CID	765
UNII	12133JR80S Y
CompTox Dashboard (EPA)	DTXSID00893055
InChI InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1 Y Key: NYHBQMYGNKIUIF-UUOKFMHZSA-N Y InChI=1/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1 Key: NYHBQMYGNKIUIF-UUOKFMHZBU
SMILES c1nc2c(=O)[nH]c(nc2n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
Properties
Chemical formula	C10H13N5O5
Molar mass	283.241
Appearance	white, crystalline powder[2]
Odor	odorless[2]
Melting point	239 (decomposes)[3]
Magnetic susceptibility (χ)	-149.1·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Guanosine (symbol G or Guo) 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.

Physical and chemical properties

Guanosine is a white, crystalline powder with no odor and mild saline taste.^[2] It is very soluble in acetic acid, slightly soluble in water, insoluble in ethanol, diethyl ether, benzene and chloroform.^[3]

Functions

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.^[4]

Uses

The antiviral drug acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are structurally similar to guanosine.^[5][6] Guanosine was also used to make regadenoson.

Sources

Guanosine can be found in pancreas, clover, coffee plant, and pollen of pines.^[2]