Guanosine

Guanosine

Names
IUPAC name 2-Amino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-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
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
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 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 acyclovir, often used in herpes treatment, and the anti-HIV drug abacavir, are 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

Guanosine was used to make Regadenoson.

References