グアニル酸
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/08/05 02:02:28」(JST)
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Not to be confused with Cyclic guanosine monophosphate.
Guanosine monophosphate
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Names |
IUPAC name
[(2R,3S,4R,5R)-5-(2-Amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate[citation needed]
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Other names
5'-Guanidylic acid,
5'-Guanylic acid,
E number E626
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Identifiers |
CAS Registry Number
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85-32-5 Y |
Abbreviations |
GMP |
ChEMBL |
ChEMBL604603 N |
IUPHAR/BPS
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5123 |
Jmol-3D images |
Image |
MeSH |
Guanosine+monophosphate |
PubChem |
6804 |
SMILES
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C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)NC(=NC2=O)N
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Properties |
Chemical formula
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C10H14N5O8P |
Molar mass |
363.22 g/mol |
Acidity (pKa) |
0.7, 2.4, 6.1, 9.4 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is: Y/N?) |
Infobox references |
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This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (April 2010) |
Guanosine monophosphate, also known as 5'-guanidylic acid or guanylic acid and abbreviated GMP, 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.[1]
Guanosine monophosphate in the form of its salts, such as disodium guanylate (E627), dipotassium guanylate (E628) and calcium guanylate (E629), are food additives used as flavor enhancers to provide the umami taste. It is often used in synergy with disodium inosinate; the combination is known as disodium 5'-ribonucleotides. Disodium guanylate is often found in instant noodles, potato chips and snacks, savoury rice, tinned vegetables, cured meats, and packet soup.
As it is a fairly expensive additive, it is usually not used independently of glutamic acid or monosodium glutamate (MSG), which also contribute umami. If inosinate and guanylate salts are present in a list of ingredients but MSG does not appear to be, the glutamic acid is likely provided as part of another ingredient, such as a processed soy protein complex (hydrolyzed soy protein), autolyzed yeast or soy sauce.
As inhibitor of guanosine monophosphate synthesis in experimental models, the glutamine analogue DON can be used.[2]
As an acyl substituent, it takes the form of the prefix guanylyl-.
See also
- Hypoxanthine-guanine phosphoribosyltransferase
- Ribonucleoside
- Umami
References
- ^ http://www.vrg.org/blog/2011/03/21/disodium-inosinate-and-disodium-guanylate-are-all-vegetable-flavor-enhancers/
- ^ Ahluwalia GS et al. Metabolism and action of amino acid analog anti-cancer agents ”, in Pharmac. Ther. (1990) 46: 243-271
Nucleic acid constituents
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Nucleobase |
- Purine
- Adenine
- Guanine
- Hypoxanthine
- Xanthine
- Purine analogue
- Pyrimidine
- Uracil
- Thymine
- Cytosine
- Pyrimidine analogue
- Unnatural base pair (UBP)
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Nucleoside |
Ribonucleoside |
- Adenosine
- Guanosine
- 5-Methyluridine
- Uridine
- Cytidine
- Inosine
- Xanthosine
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Deoxyribonucleoside |
- Deoxyadenosine
- Deoxyguanosine
- Thymidine
- Deoxyuridine
- Deoxycytidine
- Deoxyinosine
- Deoxyxanthosine
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Nucleotide
(Nucleoside monophosphate) |
Ribonucleotide |
- AMP
- GMP
- m5UMP
- UMP
- CMP
- IMP
- XMP
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Deoxyribonucleotide |
- dAMP
- dGMP
- dTMP
- dUMP
- dCMP
- dIMP
- dXMP
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Cyclic nucleotide |
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Nucleoside diphosphate |
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Nucleoside triphosphate |
- ATP
- GTP
- m5UTP
- UTP
- CTP
- ITP
- XTP
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- dATP
- dGTP
- dTTP
- dUTP
- dCTP
- dITP
- dXTP
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Index of biochemical families
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Carbohydrates |
- Alcohols
- Glycoproteins
- Glycosides
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Lipids |
- Eicosanoids
- Fatty acids
- Glycerides
- Phospholipids
- Sphingolipids
- Steroids
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Nucleic acids |
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Proteins |
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Other |
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UpToDate Contents
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English Journal
- Initial studies on the direct and modulatory effects of nitric oxide on an identified central Helix aspersa neuron.
- Wright NJ1, Sides LJ, Walling K.
- Invertebrate neuroscience : IN.Invert Neurosci.2015 Mar;15(1):175. doi: 10.1007/s10158-014-0175-3. Epub 2014 Nov 8.
- The generation of the novel messenger molecule nitric oxide (NO) has been demonstrated in many tissues across phyla including nervous systems. It is produced on demand by the enzyme nitric oxide synthase often stimulated by intracellular calcium and typically affecting guanylate cyclase thought to b
- PMID 25380983
- The beta-3 adrenoceptor agonist, mirabegron relaxes isolated prostate from human and rabbit: New therapeutic indication?
- Calmasini FB1, Candido TZ, Alexandre EC, D'Ancona CA, Silva D, de Oliveira MA, De Nucci G, Antunes E, Mónica FZ.
- The Prostate.Prostate.2015 Mar;75(4):440-7. doi: 10.1002/pros.22930. Epub 2014 Nov 21.
- BACKGROUND: Alpha1 (α1)-blockers, 5-alpha reductase and phosphodiesterase type-5 inhibitors are pharmacological classes currently available for benign prostatic hyperplasia (BPH) treatment. Mirabegron, a beta-3 adrenoceptor (β3-AR) agonist has been approved for the therapy of overactive bladder an
- PMID 25417911
- GTP is an allosteric modulator of the interaction between the guanylate-binding protein 1 and the prosurvival kinase PIM1.
- Persico M1, Petrella L2, Orteca N1, Di Dato A1, Mariani M3, Andreoli M3, De Donato M4, Scambia G4, Novellino E1, Ferlini C5, Fattorusso C6.
- European journal of medicinal chemistry.Eur J Med Chem.2015 Feb 16;91:132-44. doi: 10.1016/j.ejmech.2014.07.093. Epub 2014 Jul 27.
- GBP1 and PIM1 are known to interact with a molar ratio 1:1. GBP1:PIM1 binding initiates a signaling pathway that induces resistance to common chemotherapeutics such as paclitaxel. Since GBP1 is a large GTPase which undergoes conformational changes in a nucleotide-dependent manner, we investigated th
- PMID 25081641
Japanese Journal
- Neuroprotective effect of nitrite-derived NO in brain injury mediated through the NOS-independent but not the GC/COX/xanthine oxidase/PGIS-dependent pathways
- 無脊椎動物神経系を用いた非連合学習の分子メカニズムの解明
- Novel Therapies for Heart Failure – Where Do They Stand? –
Related Links
- guanylate (plural guanylates) (biochemistry) any salt or ester of guanylic acid; the salts are used as flavour enhancers Translations [edit] salt or ester of guanylic acid German: Guanylat n Retrieved from "https://en.wiktionary.org" ...
- Details on Disodium Guanylate and its health effects ... Alternate Names Disodium 5' -guanylate, Sodium 5' -guanylate Description A flavor enhancer/intensifier that is almost always used in conjunction with MSG and sometimes disodium inosinate ...
Related Pictures
★リンクテーブル★
[★]
- 関
- 5'-guanylic acid、GMP、guanosine monophosphate、guanylate
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- 英
- guanylate, guanylic acid
- 関
- グアノシン一リン酸 GMP
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グアニル酸シクラーゼ活性化タンパク質
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