Guanosine
| Names | |
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| IUPAC name
Guanosine[1]
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| 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
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| Identifiers | |
3D model (JSmol)
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| KEGG | |
| MeSH | Guanosine |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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
[edit | edit source]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
[edit | edit source]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
[edit | edit source]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
[edit | edit source]Guanosine can be found in pancreas, clover, coffee plant, and pollen of pines.[2]
References
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- ^ Product Information: ZIAGEN(R) oral tablets, oral solution, abacavir sulfate oral tablets, oral solution. ViiV Healthcare (per Manufacturer), Research Triangle Park, NC, 2015.
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