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Adenosine monophosphate

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Adenosine monophosphate
Skeletal formula of AMP
Ball-and-stick model of AMP
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.455 Edit this at Wikidata
KEGG
MeSH Adenosine+monophosphate
UNII
  • 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 checkY
    Key: UDMBCSSLTHHNCD-KQYNXXCUSA-N checkY
  • 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
  • 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
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[citation needed], 3.8, 6.1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

AMP plays an important role in many cellular metabolic processes, being interconverted to ADP and/or ATP. AMP is used as a monomer in the synthesis of RNA.

Production and degradation

AMP does not have the high energy pyrophosphate bond associated with ADP and ATP. AMP can be produced from ADP:

2 ADP → ATP + AMP

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

ADP + H2O → AMP + Pi

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

ATP + H2O → 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)

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.

See also

References

  • 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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