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Guanosine

From Wikipedia, in a visual modern way
Guanosine
Skeletal formula of guanosine
Ball-and-stick model of the guanosine molecule
Names
IUPAC name
Guanosine[1]
Preferred 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
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).
checkY verify (what is checkY☒N ?)
Not to be confused with Guanine, Guanidine, Guanfacine, or Guanamine.

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.

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Nucleoside

Nucleoside

Nucleosides are glycosylamines that can be thought of as nucleotides without a phosphate group. A nucleoside consists simply of a nucleobase and a five-carbon sugar whereas a nucleotide is composed of a nucleobase, a five-carbon sugar, and one or more phosphate groups. In a nucleoside, the anomeric carbon is linked through a glycosidic bond to the N9 of a purine or the N1 of a pyrimidine. Nucleotides are the molecular building blocks of DNA and RNA.

Guanine

Guanine

Guanine is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine. In DNA, guanine is paired with cytosine. The guanine nucleoside is called guanosine.

Glycosidic bond

Glycosidic bond

A glycosidic bond or glycosidic linkage is a type of ether bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate.

Phosphorylation

Phosphorylation

In biochemistry, phosphorylation is the attachment of a phosphate group to a molecule or an ion. This process and its inverse, dephosphorylation, are common in biology and could be driven by natural selection. Protein phosphorylation often activates many enzymes.

Guanosine monophosphate

Guanosine monophosphate

Guanosine monophosphate (GMP), also known as 5′-guanidylic acid or guanylic acid, is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside guanosine. GMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase guanine; hence it is a ribonucleoside monophosphate. Guanosine monophosphate is commercially produced by microbial fermentation.

Cyclic guanosine monophosphate

Cyclic guanosine monophosphate

Cyclic guanosine monophosphate (cGMP) is a cyclic nucleotide derived from guanosine triphosphate (GTP). cGMP acts as a second messenger much like cyclic AMP. Its most likely mechanism of action is activation of intracellular protein kinases in response to the binding of membrane-impermeable peptide hormones to the external cell surface.

Guanosine diphosphate

Guanosine diphosphate

Guanosine diphosphate, abbreviated GDP, is a nucleoside diphosphate. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of a pyrophosphate group, a pentose sugar ribose, and the nucleobase guanine.

Guanosine triphosphate

Guanosine triphosphate

Guanosine-5'-triphosphate (GTP) is a purine nucleoside triphosphate. It is one of the building blocks needed for the synthesis of RNA during the transcription process. Its structure is similar to that of the guanosine nucleoside, the only difference being that nucleotides like GTP have phosphates on their ribose sugar. GTP has the guanine nucleobase attached to the 1' carbon of the ribose and it has the triphosphate moiety attached to ribose's 5' carbon.

Nucleic acid

Nucleic acid

Nucleic acids are biopolymers, macromolecules, essential to all known forms of life. They are composed of nucleotides, which are the monomer components: a 5-carbon sugar, a phosphate group and a nitrogenous base. The two main classes of nucleic acids are deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). If the sugar is ribose, the polymer is RNA; if the sugar is the ribose derivative deoxyribose, the polymer is DNA.

Photosynthesis

Photosynthesis

Photosynthesis is a process used by plants and other organisms to convert light energy into chemical energy that, through cellular respiration, can later be released to fuel the organism's activities. Some of this chemical energy is stored in carbohydrate molecules, such as sugars and starches, which are synthesized from carbon dioxide and water – hence the name photosynthesis, from the Greek phōs, "light", and synthesis, "putting together". Most plants, algae, and cyanobacteria perform photosynthesis; such organisms are called photoautotrophs. Photosynthesis is largely responsible for producing and maintaining the oxygen content of the Earth's atmosphere, and supplies most of the energy necessary for life on Earth.

Deoxyribose

Deoxyribose

Deoxyribose, or more precisely 2-deoxyribose, is a monosaccharide with idealized formula H−(C=O)−(CH2)−(CHOH)3−H. Its name indicates that it is a deoxy sugar, meaning that it is derived from the sugar ribose by loss of a hydroxy group. Discovered in 1929 by Phoebus Levene, deoxyribose is most notable for its presence in DNA. Since the pentose sugars arabinose and ribose only differ by the stereochemistry at C2′, 2-deoxyribose and 2-deoxyarabinose are equivalent, although the latter term is rarely used because ribose, not arabinose, is the precursor to deoxyribose.

Deoxyguanosine

Deoxyguanosine

Deoxyguanosine is composed of the purine nucleobase guanine linked by its N9 nitrogen to the C1 carbon of deoxyribose. It is similar to guanosine, but with one hydroxyl group removed from the 2' position of the ribose sugar. If a phosphate group is attached at the 5' position, it becomes deoxyguanosine monophosphate.

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]

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Acetic acid

Acetic acid

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

Ethanol

Ethanol

Ethanol is an organic compound. It is an alcohol with the chemical formula C2H6O. Its formula can also be written as CH3−CH2−OH or C2H5OH. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, and the active ingredient in alcoholic drinks.

Diethyl ether

Diethyl ether

Diethyl ether, or simply ether, is an organic compound in the ether class with the formula (CH3CH2)2O or (C2H5)2O, sometimes abbreviated as Et2O, where Et stands for monovalent ethyl group CH3CH2 which is often written as C2H5. It is a colourless, highly volatile, sweet-smelling, extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication.

Benzene

Benzene

Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

Chloroform

Chloroform

Chloroform, or trichloromethane (often abbreviated as TCM), is an organic compound with the formula CHCl3 and a common organic solvent. It is a very volatile, colorless, strong-smelling, dense liquid produced on a large scale as a precursor to PTFE and refrigerants and is a trihalomethane that serves as a powerful anesthetic, euphoriant, anxiolytic, and sedative when inhaled or ingested. It is also part of a wider class of substances known as volatile organic compounds.

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
Guanosine with numbered carbons

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RNA splicing

RNA splicing

RNA splicing is a process in molecular biology where a newly-made precursor messenger RNA (pre-mRNA) transcript is transformed into a mature messenger RNA (mRNA). It works by removing all the introns and splicing back together exons. For nuclear-encoded genes, splicing occurs in the nucleus either during or immediately after transcription. For those eukaryotic genes that contain introns, splicing is usually needed to create an mRNA molecule that can be translated into protein. For many eukaryotic introns, splicing occurs in a series of reactions which are catalyzed by the spliceosome, a complex of small nuclear ribonucleoproteins (snRNPs). There exist self-splicing introns, that is, ribozymes that can catalyze their own excision from their parent RNA molecule. The process of transcription, splicing and translation is called gene expression, the central dogma of molecular biology.

Intron

Intron

An intron is any nucleotide sequence within a gene that is not expressed or operative in the final RNA product. The word intron is derived from the term intragenic region, i.e. a region inside a gene. The term intron refers to both the DNA sequence within a gene and the corresponding RNA sequence in RNA transcripts. The non-intron sequences that become joined by this RNA processing to form the mature RNA are called exons.

Exon

Exon

An exon is any part of a gene that will form a part of the final mature RNA produced by that gene after introns have been removed by RNA splicing. The term exon refers to both the DNA sequence within a gene and to the corresponding sequence in RNA transcripts. In RNA splicing, introns are removed and exons are covalently joined to one another as part of generating the mature RNA. Just as the entire set of genes for a species constitutes the genome, the entire set of exons constitutes the exome.

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.

Source: "Guanosine", Wikipedia, Wikimedia Foundation, (2021, September 15th), https://en.wikipedia.org/wiki/Guanosine.

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Further Reading

Nucleotide

Purine

Cytidine

Cyclic nucleotide

Biomolecule

Ribonucleotide

Guanylate cyclase

Aciclovir

Hypoxanthine-guanine phosphoribosyltransferase

Guanosine monophosphate

Nucleic acid metabolism

Capping enzyme

GMP synthase

GMP reductase
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. p. 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.
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