| 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
|3D model (Jmol)|| Interactive image|
|Molar mass||347.22 g/mol|
|Appearance||white crystalline powder|
|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).
|(what is ?)|
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
- 2 ADP → ATP + AMP
- ADP → AMP + Pi
- ATP → AMP + PPi
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 + Pi → ATP (this step is most often performed in aerobes by the ATP synthase during oxidative phosphorylation)
In a catabolic pathway, adenosine monophosphate can be converted to uric acid, which is excreted from the body.
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.
- 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.