Adenosine monophosphate

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 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:16027 Y
ChemSpider	5858 Y
DrugBank	DB00131 Y
ECHA InfoCard	100.000.455
IUPHAR/BPS	2455
KEGG	C00020 Y
MeSH	Adenosine+monophosphate
PubChem CID	6083
UNII	415SHH325A Y
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 Y Key: UDMBCSSLTHHNCD-KQYNXXCUSA-N Y 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).
N verify (what is YN ?)
Infobox references

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, which does not have the typical high energy bond of the so-called adenosine monophosphate ("AMP") that arises on the hydrolysis of ATP. 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.

See also

• DNA
• Oligonucleotide
• Phosphodiesterase

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. PMC 22308 . PMID 10449792. doi:10.1073/pnas.96.17.9903.