Guanosine

Not to be confused with Guanine, Guanidine, Guanfacine, or Guanamine.
Guanosine
Skeletal formula of guanosine
Ball-and-stick model of the guanosine molecule
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.844 Edit this at Wikidata
KEGG
MeSH Guanosine
UNII
  • 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 checkY
    Key: NYHBQMYGNKIUIF-UUOKFMHZSA-N checkY
  • 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
  • c1nc2c(=O)[nH]c(nc2n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
Properties
C10H13N5O5
Molar mass 283.241
Appearance white, crystalline powder[2]
Odor odorless[2]
Melting point 239 (decomposes)[3]
-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).
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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]

Guanosine with numbered carbons

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]

References

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1421. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ a b c d Robert A. Lewis, Michael D. Larrañaga, Richard J. Lewis Sr. (2016). Hawley's Condensed Chemical Dictionary (16th ed.). Hoboken, New Jersey: John Wiley & Sons, Inc. p. 688. ISBN 978-1-118-13515-0.{{cite book}}: CS1 maint: multiple names: authors list (link)
  3. ^ a b William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. pp. 3–286. ISBN 978-1-4987-5429-3.
  4. ^ Splicing (JPG) Archived June 13, 2010, at the Wayback Machine
  5. ^ "Acyclovir". The American Society of Health-System Pharmacists. Archived from the original on 2015-01-05. Retrieved Jan 1, 2015.
  6. ^ Product Information: ZIAGEN(R) oral tablets, oral solution, abacavir sulfate oral tablets, oral solution. ViiV Healthcare (per Manufacturer), Research Triangle Park, NC, 2015.