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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/07 22:59:47」(JST)

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Adenosine monophosphate (AMP), also known as 5'-adenylic acid, is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid and the nucleoside adenosine. AMP consists of a phosphate group, the sugar ribose, and the nucleobase adenine. As a substituent it takes the form of the prefix adenylyl-.

Production and degradation

AMP can be produced during ATP synthesis by the enzyme adenylate kinase by combining two ADP molecules:

2 ADP → ATP + AMP

Or AMP may be produced by the hydrolysis of one high energy phosphate bond of ADP:

ADP → AMP + P_i

AMP can also be formed by hydrolysis of ATP into AMP and pyrophosphate:

ATP → AMP + PP_i

When RNA is broken down by living systems, nucleoside monophosphates, including adenosine monophosphate, are formed.

AMP can be regenerated to ATP as follows:

AMP + ATP → 2 ADP (adenylate kinase in the opposite direction)

ADP + P_i → ATP (this step is most often performed in aerobes by the ATP synthase during oxidative phosphorylation)

AMP can be converted into IMP by the enzyme myoadenylate deaminase, freeing an ammonia group.

In a catabolic pathway, adenosine monophosphate can be converted to uric acid, which is excreted from the body.

cAMP

AMP can also exist as a cyclic structure known as cyclic AMP (or cAMP). Within certain cells the enzyme adenylate cyclase makes cAMP from ATP, and typically this reaction is regulated by hormones such as adrenaline or glucagon. cAMP plays an important role in intracellular signaling.

References

External links

GMD MS Spectrum
Ming D, Ninomiya Y, Margolskee RF (1999). "Blocking taste receptor activation of gustducin inhibits gustatory responses to bitter compounds". Proc. Natl. Acad. Sci. USA 96 (17): 9903–9908. doi:10.1073/pnas.96.17.9903. PMC 22308. PMID 10449792.

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English Journal

Cross-talk in nucleotide signaling in glioma c6 cells.

Wypych D, Barańska J.SourceNencki Institute of Experimental Biology, Polish Academy of Sciences, 3 Pasteur St, PL 02-093, Warsaw, Poland, d.wypych@nencki.gov.pl.
Advances in experimental medicine and biology.Adv Exp Med Biol.2013;986:31-59.
The chapter is focused on the mechanism of action of metabotropic P2Y nucleotide receptors: P2Y(1), P2Y(2), P2Y(12), P2Y(14) and the ionotropic P2X(7) receptor in glioma C6 cells. P2Y(1) and P2Y(12) both respond to ADP, but while P2Y(1) links to PLC and elevates cytosolic Ca(2+) concentration, P2Y(1
PMID 22879063

Control of Oocyte Growth and Meiotic Maturation in Caenorhabditis elegans.

Kim S, Spike C, Greenstein D.SourceDepartment of Genetics, Cell Biology, and Development, University of Minnesota, Minneapolis, MN, 55455, USA.
Advances in experimental medicine and biology.Adv Exp Med Biol.2013;757:277-320.
In sexually reproducing animals, oocytes arrest at diplotene or diakinesis and resume meiosis (meiotic maturation) in response to hormones. Chromosome segregation errors in female meiosis I are the leading cause of human birth defects, and age-related changes in the hormonal environment of the ovary
PMID 22872481

Japanese Journal

TGF-β Decreases the Stability of IL-18-Induced IFN-γ mRNA through the Expression of TGF-β-Induced Tristetraprolin in KG-1 Cells

Inoue Yasumichi,Abe Kenji,Onozaki Kikuo [他],Hayashi Hidetoshi
Biological and Pharmaceutical Bulletin 38(4), 536-544, 2015
… The stability of IFN-γ mRNA was regulated by mRNA destabilizing elements in the 3′untranslated region (UTR) of IFN-γ mRNA, especially adenylate-uridylate (AU)-rich elements (AREs) in the 5′ half of 3′UTR. …
NAID 130005062261

ストリング法によるタンパク質構造変化解析 (特集生体高分子の揺らぎとダイナミクス : シミュレーションと実験の統計解析)

松永康佑
統計数理 62(2), 285-299, 2014-12
NAID 40020364194

Immunohistochemical Study on Glucagon-Like Peptide-1 (GLP-1) and Pituitary Adenylate Cyclase Activating Peptide (PACAP) in the Small Intestine of Muscovy Duck during the Prehatching and Posthatching Periods

Ding Baoan,Lenzi Carla,Pirone Andrea
Journal of poultry science 51(1), 35-41, 2014-01
NAID 40019956444

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★リンクテーブル★

リンク元	「アデノシン一リン酸」「アデニル化」「adenylation」
拡張検索	「polyadenylated RNA」「polyadenylate」「pituitaryadenylate cyclase-activating polypeptide receptor」「adenylate cyclase toxin」「adenylate cyclase」

「アデノシン一リン酸」

Adenosine monophosphate
Names
	IUPAC name [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
	Other names Adenosine 5'-monophosphate, 5'-Adenylic acid
Identifiers
CAS Number	61-19-8
ChEBI	CHEBI:16027
ChEMBL	ChEMBL752
ChemSpider	5858
DrugBank	DB00131
IUPHAR/BPS	2455
Jmol 3D model	Interactive image; Interactive image
KEGG	C00020
MeSH	Adenosine+monophosphate
PubChem	6083
UNII	415SHH325A
	InChI InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1 Key: UDMBCSSLTHHNCD-KQYNXXCUSA-N ; InChI=1/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1 Key: UDMBCSSLTHHNCD-KQYNXXCUBP ;
	SMILES O=P(O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O ; c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N ;
Properties
Chemical formula	C10H14N5O7P
Molar mass	347.22 g/mol
Appearance	white crystalline powder
Density	2.32 g/mL
Melting point	178 to 185 °C (352 to 365 °F; 451 to 458 K)
Boiling point	798.5 °C (1,469.3 °F; 1,071.7 K)
Acidity (pKa)	0.9, 3.8, 6.1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references