Adenosine monophosphate
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{{Chembox new
| ImageFile = AMP structure.svg
| ImageSize = 300px
| IUPACName = 5'-Adenylic acid
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 61-19-8
| PubChem =
| 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
| 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 g/mol
| Appearance =
| Density =
| MeltingPt =
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| Section3 = {{Chembox Hazards
| Solubility =
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}}
'''Adenosine monophosphate''', also known as '''5'-adenylic acid''' and abbreviated '''AMP''', is a [[nucleotide]] that is found in [[RNA]]. It is an [[ester]] of [[phosphoric acid]] with the [[nucleoside]] [[adenosine]]. AMP consists of the [[phosphate]] [[Functional group|group]], the [[pentose]] [[sugar]] [[ribose]], and the [[nucleobase]] [[adenine]].
==Production and degradation==
AMP can be produced during [[Adenosine triphosphate|ATP]] synthesis by the enzyme [[adenylate kinase]] by combining two [[Adenosine diphosphate|ADP]] molecules:
: 2 ADP → ATP + AMP''
Or AMP may be produced by the [[hydrolysis]] of one [[high energy phosphate]] bond of ADP:
: ADP → AMP + [[phosphate|P<sub>i</sub>]]
AMP can also be formed by hydrolysis of [[Adenosine triphosphate|ATP]] into AMP and [[pyrophosphate]]:
: ATP → AMP + [[pyrophosphate|PP<sub>i</sub>]]
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<sub>i</sub> → ATP (this step is most often performed in aerobes by the [[ATP synthase]] during [[oxidative phosphorylation]])
AMP can be converted into [[inosine monophosphate|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 adenosine monophosphate|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.
==Application as a bitterness suppressor==
To human tastes, the bitterness-suppressing quality of AMP interprets as food seeming 'sweeter'. This makes lower-calorie food products more palatable, making AMP potentially a lucrative solution for food manufacturers as they respond to pressure from consumers and regulators concerned about social trends towards [[obesity]].<ref>[http://www.google.com/patents?vid=USPAT6942874&id=5a0VAAAAEBAJ&dq=6942874 Nucleotide compounds that block the bitter taste of oral compositions] patent by [[Linguagen Corp]])</ref> AMP has been approved by the [[Food and Drug Administration]] as a 'Bitter Blocker' additive to foodstuffs.<ref>[http://www.drugresearcher.com/news/ng.asp?id=54804-bitter-blocker-backed Bitter Blocker Backed]</ref>
==See also==
* [[DNA]]
* [[Oligonucleotide]]
==References==
<references/>
==External links==
* [http://www.compchemwiki.org/index.php?title=Adenosine_monophosphate Computational Chemistry Wiki]
* [http://www.pnas.org/cgi/content/full/96/17/9903 Blocking taste receptor activation of gustducin inhibits gustatory responses to bitter compounds]
{{Nucleobases, nucleosides, and nucleotides}}
[[Category:Nucleotides]]
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