Guanosine

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Not to be confused with Guanine, Guanidine, or Guanfacine.
Guanosine
Skeletal formula of guanosine
Ball-and-stick model of the guanosine molecule
Names
IUPAC name
2-Amino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
Other names
Guanine riboside
Identifiers
118-00-3 YesY
ChEBI CHEBI:16750 YesY
ChEMBL ChEMBL375655 YesY
ChemSpider 6544 YesY
DrugBank DB02857 YesY
4567
Jmol-3D images Image
KEGG C00387 YesY
MeSH Guanosine
PubChem 765
UNII 12133JR80S YesY
Properties
C10H13N5O5
Molar mass 283.241
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what isYesY/N?)
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, 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

References[edit]

  1. ^ Splicing (JPG) Archived June 13, 2010 at the Wayback Machine