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Adenosine monophosphate

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
61-19-8 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:16027 YesY
ChEMBL ChEMBL752 YesY
ChemSpider 5858 YesY
DrugBank DB00131 YesY
ECHA InfoCard 100.000.455
2455
KEGG C00020 YesY
MeSH Adenosine+monophosphate
PubChem 6083
UNII 415SHH325A YesY
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, 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  (what is YesYN ?)
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, wich 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-.

AMP can be produced during ATP synthesis by the enzyme adenylate kinase by combining two ADP molecules:

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

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

When RNA is broken down by living systems, nucleoside monophosphates, including adenosine monophosphate, are formed.

AMP can be regenerated to ATP as follows:

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.

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.


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Wikipedia

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