查看“︁單磷酸腺苷”︁的源代码

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{{redirect|腺苷酸}}
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|G2=Chemistry
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{{Chembox
| Name = 單磷酸腺苷
| ImageFile = AMP_chemical_structure.png
| ImageFile1 = Adenosine-monophosphate-3D-spacefill.png
| IUPACNameZh = 5'-腺嘌呤核苷酸
| Abbreviations = AMP
| Section1 = {{Chembox Identifiers
|   CASNo = 61-19-8
|   CASNo_Ref = {{cascite|correct|CAS}}
|   SMILES  =  O[C@H]1[C@H]([C@@H]</br/>(O[C@@H]1COP(O)(O)=O)</br/>N2C3=C(N=C2)C(N)=NC=N3)O

| PubChem = 6083
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5858
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 415SHH325A
| 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
| InChIKey = UDMBCSSLTHHNCD-KQYNXXCUBP
| SMILES1 = c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 752
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UDMBCSSLTHHNCD-KQYNXXCUSA-N
| IUPHAR_ligand = 2455
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00131
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16027
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00020
| SMILES2 = O=P(O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O
| MeSHName = Adenosine+monophosphate
}}
| Section2 = {{Chembox Properties
|   Formula = C<sub>10</sub>H<sub>14</sub>N<sub>5</sub>O<sub>7</sub>P
|   MolarMass = 347.22
| Appearance = 白色粉末晶體
| pKa = 0.9, 3.8, 6.1
| Density = 2.32 g/mL
| MeltingPt = 178-185 °C（451-458 K）
| BoilingPtC = 798.5
  }}
}}
'''單磷酸腺苷'''（英文：'''Adenosine monophosphate'''，簡稱'''AMP'''），又名'''5'-腺嘌呤核苷酸'''或'''腺苷酸'''，是一種在[[核糖核酸]]（RNA）中發現的[[核苷酸]]。它是一種[[磷酸]]及[[核苷]][[腺苷]]的[[酯]]，並由[[磷酸鹽]][[官能团]]、[[戊糖]][[核糖]]及[[核鹼基|鹼基]][[腺嘌呤]]所組成。<ref>[http://myhealth.barnesjewish.org/library/healthguide/en-us/Cam/topic.asp?hwid=hn-2796008 Barnes-Jewish Hospital, 2005, Adenosine Monophosphate (於2006年9月27日查閱)]{{dead link|date=2017年12月 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>

== 生產及降解 ==
單磷酸腺苷可以從[[腺苷酸激酶]]催化兩個[[二磷酸腺苷]]（ADP）分子合成[[三磷酸腺苷]]（ATP）時生成：

:<math>2\mbox{ADP} \rightarrow \mbox{ATP} + \mbox{AMP}</math>

或是經由[[水解]]ADP的[[高能磷酸鍵]]生成：

:<math>\mbox{ADP} \rightarrow \mbox{AMP} + \mbox{P}_{\mbox{i}}</math>

水解ATP亦可生成AMP及[[焦磷酸鹽]]：

:<math>\mbox{ATP} \rightarrow \mbox{AMP} + \mbox{PP}_{\mbox{i}}</math>

當[[核糖核酸]]（RNA）被分解後，一磷酸[[核苷]]，包括一磷酸腺苷會被生成。

而AMP可以從以下的方式再生成ATP：

:<math>\mbox{AMP} + \mbox{ATP} \rightarrow 2\mbox{ADP}</math>（腺苷酸激酶在另一方向）

:<math>2\mbox{ADP} + 2\mbox{P}_{\mbox{i}} \rightarrow 2\mbox{ATP}</math>（此一步驟是經常被好氧性生物的[[三磷酸腺苷合成酶]]在[[氧化磷酸化]]採用）

AMP亦可由[[肌腺苷酸脫胺酶]]釋放一組[[氨]]基轉為[[一磷酸肌苷]]。

在分解代謝的過程中，AMP可以轉化成為[[尿酸]]排出體外。

== 環磷酸腺苷 ==
:{{main|環磷酸腺苷}}
AMP亦可有一種環狀結構稱為[[環磷酸腺苷]]（或稱為cAMP）。在某些[[細胞]]由[[腺苷環化酶]]催化ATP成為cAMP，並一般由[[腎上腺素]]或[[胰高血糖素]]所調節。cAMP在細胞內的訊息傳遞起著重要的角色。

== 商業應用 ==
另外，AMP在對[[人類]]測試後，有著壓抑苦味的特性，使得食物仿佛甜些。這種發現可以使得低[[卡路里]]食物更美味，在對[[肥胖症]]擔心的時間，成為改善食物質素的較有益方法。這種特性於2004年9月已經得到[[美國食品藥物管理局]]的批准，由[[美國]][[紐澤西州]]的[[靈瓜金]]以AMP作為食品的苦味遮罩的專利。<ref>{{cite web |url=http://www.linguagen.com/home_flash.shtml |title=存档副本 |accessdate=2006-09-27 |deadurl=yes |archiveurl=https://web.archive.org/web/20061105000900/http://www.linguagen.com/home_flash.shtml |archivedate=2006-11-05 }} '''靈瓜金'''官方網頁</ref>

== 內部連結 ==
*[[核苷]]
*[[核苷酸]]
*[[脫氧核糖核酸]]
*[[核糖核酸]]
*[[寡核苷酸]]
=== 核糖核苷酸 ===

{|
|- align="center" valign="bottom"
| [[File:AMP chemical structure.png|126px|Chemical structure of adenosine monophosphate]]<br />單磷酸腺苷<br />AMP
| [[File:ADP chemical structure.png|156px|Chemical structure of adenosine diphosphate]]<br />[[二磷酸腺苷]]<br />ADP
| [[File:ATP structure revised.svg|186px|Chemical structure of adenosine triphosphate]]<br />[[三磷酸腺苷]]<br />ATP
|- align="center" valign="bottom"
| [[File:GMP chemical structure.png|154px|Chemical structure of guanosine monophosphate]]<br />[[單磷酸鳥苷]]<br />GMP
| [[File:GDP chemical structure.png|184px|Chemical structure of guanosine diphosphate]]<br />[[二磷酸鳥苷]]<br />GDP
| [[File:GTP chemical structure.png|214px|Chemical structure of guanosine triphosphate]]<br />[[三磷酸鳥苷]]<br />GTP
|- align="center" valign="bottom"
| [[File:TMP chemical structure.png|117px|Chemical structure of thymidine monophosphate]]<br />[[單磷酸胸苷]]<br />TMP
| [[File:TDP chemical structure.png|148px|Chemical structure of thymidine diphosphate]]<br />[[二磷酸胸苷]]<br />TDP
| [[File:TTP chemical structure.png|178px|Chemical structure of thymidine triphosphate]]<br />[[三磷酸胸苷]]<br />TTP
|- align="center" valign="bottom"
| [[File:UMP chemical structure.png|117px|Chemical structure of uridine monophosphate]]<br />[[单磷酸尿苷]]<br />UMP
| [[File:UDP chemical structure.png|148px|Chemical structure of uridine diphosphate]]<br />[[二磷酸尿苷]]<br />UDP
| [[File:UTP chemical structure.png|178px|Chemical structure of uridine triphosphate]]<br />[[三磷酸尿苷]]<br />UTP
|- align="center" valign="bottom"
| [[File:CMP chemical structure.png|117px|Chemical structure of cytidine monophosphate]]<br />[[單磷酸胞苷]]<br />CMP
| [[File:CDP chemical structure.png|148px|Chemical structure of cytidine diphosphate]]<br />[[二磷酸胞苷]]<br />CDP
| [[File:CTP chemical structure.png|178px|Chemical structure of cytidine triphosphate]]<br />[[三磷酸胞苷]]<br />CTP
|-
|}

=== 脫氧核糖核苷酸 ===

{|
|- align="center" valign="bottom"
| [[File:dAMP chemical structure.png|126px|Chemical structure of deoxyadenosine monophosphate]]<br />[[單磷酸脫氧腺苷]]<br />dAMP
| [[File:dADP chemical structure.png|156px|Chemical structure of deoxyadenosine diphosphate]]<br />[[二磷酸脫氧腺苷]]<br />dADP
| [[File:dATP chemical structure.png|186px|Chemical structure of deoxyadenosine triphosphate]]<br />[[三磷酸脫氧腺苷]]<br />dATP
|- align="center" valign="bottom"
| [[File:dGMP chemical structure.png|154px|Chemical structure of deoxyguanosine monophosphate]]<br />[[單磷酸脫氧鳥苷]]<br />dGMP
| [[File:dGDP chemical structure.png|184px|Chemical structure of deoxyguanosine diphosphate]]<br />[[二磷酸脫氧鳥苷]]<br />dGDP
| [[File:dGTP chemical structure.png|214px|Chemical structure of deoxyguanosine triphosphate]]<br />[[三磷酸脫氧鳥苷]]<br />dGTP
|- align="center" valign="bottom"
| [[File:dTMP chemical structure.png|118px|Chemical structure of deoxythymidine monophosphate]]<br />[[單磷酸脱氧胸苷]]<br />dTMP
| [[File:dTDP chemical structure.png|148px|Chemical structure of deoxythymidine diphosphate]]<br />[[二磷酸脱氧胸苷]]<br />dTDP
| [[File:dTTP chemical structure.png|178px|Chemical structure of deoxythymidine triphosphate]]<br />[[三磷酸脱氧胸苷]]<br />dTTP
|- align="center" valign="bottom"
| [[File:dUMP chemical structure.png|118px|Chemical structure of deoxyuridine monophosphate]]<br />[[單磷酸脫氧尿苷]]<br />dUMP
| [[File:dUDP chemical structure.png|148px|Chemical structure of deoxyuridine diphosphate]]<br />[[二磷酸脫氧尿苷]]<br />dUDP
| [[File:dUTP chemical structure.png|178px|Chemical structure of deoxyuridine triphosphate]]<br />[[三磷酸脫氧尿苷]]<br />dUTP
|- align="center" valign="bottom"
| [[File:dCMP chemical structure.png|118px|Chemical structure of deoxycytidine monophosphate]]<br />[[單磷酸脫氧胞苷]]<br />dCMP
| [[File:dCDP chemical structure.png|148px|Chemical structure of deoxycytidine diphosphate]]<br />[[二磷酸脫氧胞苷]]<br />dCDP
| [[File:dCTP chemical structure.png|178px|Chemical structure of deoxycytidine triphosphate]]<br />[[三磷酸脫氧胞苷]]<br />dCTP
|-
|}

== 參考文獻 ==
{{Reflist}}

== 外部連結 ==
* [https://web.archive.org/web/20070310232615/http://www.compchemwiki.org/index.php?title=Adenosine_monophosphate Computational Chemistry Wiki]

{{碱基、核苷和核苷酸}}

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[[Category:核苷酸]]
[[Category:有機磷酸鹽]]