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Adenosine Monophosphate
CAS: 61-19-8
SKU: S3481
Adenosine Monophosphate | SKU: S3481
synonyms: 5′-Adenylic acid; Adenosine 5′-phosphate; 5′-AMP; Adenosine monophosphate; Adenylic acid; Adenosine 5′-(dihydrogen phosphate)
Adenosine Monophosphate
Adenosine 5′-monophosphate (AMP), also called 5′-adenylic acid, is the nucleotide in which a single phosphate group is esterified to the 5′-hydroxyl of adenosine (C10H14N5O7P, molecular weight 347.22 g/mol). It is a white crystalline powder that melts at about 200 °C and dissolves in water once a little alkali is added. AMP is a building unit of RNA, an intermediate in the interconversion of ATP and ADP, and the product of ATP and cyclic-AMP hydrolysis, so it sits at the centre of cellular energy metabolism. Beyond its structural role, AMP is a signalling molecule. A rising AMP:ATP ratio activates AMP-activated protein kinase (AMPK), the cell’s energy sensor: AMP promotes phosphorylation of AMPK by upstream kinases and protects it from dephosphorylation. Researchers therefore use AMP in kinase and metabolic assays. Sigma-Aldrich also lists it as a reagent for the synthesis of adenosine-5′-phosphoimidazolide, as an activator of phosphorylase b in the enzymatic synthesis of branched polysaccharides, and as an inhibitor of endogenous NMN adenylyltransferase (NMNAT) activity that converts NMN to NAD+. Sarchem Labs offers adenosine 5′-monophosphate (SKU S3481) for biochemistry, cell-biology, enzymology and nucleotide-synthesis laboratories, with a Certificate of Analysis and Safety Data Sheet for each lot. Related forms such as the monohydrate and the sodium and disodium salts have different CAS numbers and molecular weights, so please state the form you need when requesting a quote.
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Specifications

Melting Point200°C
ColorWhite
Formula Weight347.22
Physical FormCrystal-Powder at 20°C
Chemical Name or Material5′-Adenylic acid
Molecular Weight347.22 g/mol (anhydrous)
SMILES StringO[C@H]1[C@@H](O)[C@H](N(C=N2)C3=C2C(N)=NC=N3)O[C@@H]1COP(O)(O)=O
Solubility1 M NH4OH: 50 mg/mL, clear and colourless; water: soluble with addition of mild alkali
CAS Number61-19-8
Storage Temperature−20°C
Empirical FormulaC10H14N5O7P
NACRESNA.51
UNSPSC Code41106305
InChI1S/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
InChI KeyUDMBCSSLTHHNCD-KQYNXXCUSA-N
PubChem CID6083
eCl@ss32160414
FormSolid (crystal-powder at 20°C)
Related Form (Monohydrate)CAS 18422-05-4; C10H14N5O7P · H2O; 365.24 g/mol
PubChem Substance ID (monohydrate)24890637
Beilstein/REAXYS Number (monohydrate)54612
MDL Number (monohydrate)MFCD00149360

Applications

No Application Found
Enzymology and assay development: a substrate, effector or reference compound for adenylate kinase, AMP deaminase, 5′-nucleotidase and phosphodiesterase assays, where AMP is the product of cyclic-AMP hydrolysis.
Nucleotide synthesis: a starting material for chemical and enzymatic preparation of ADP, ATP, nucleotide analogues and activated derivatives such as adenosine-5′-phosphoimidazolide.
Polysaccharide biosynthesis: an activator of phosphorylase b used in the enzymatic synthesis of branched polysaccharides.
NAD+ metabolism research: an inhibitor of endogenous NMNAT activity that converts nicotinamide mononucleotide to NAD+, used in studies of NAD+ biosynthesis.
Analytical standard: a reference compound for HPLC separation and quantification of adenine nucleotides (AMP, ADP, ATP) in cell extracts, fermentation broths and food samples, for example when calculating adenylate energy charge.

Product Description

What is Adenosine 5′-Monophosphate?

Adenosine 5′-monophosphate is a ribonucleotide: adenine joined through an N9-glycosidic bond to D-ribose, which carries one phosphate group on its 5′-hydroxyl. The formula is C10H14N5O7P and the molecular weight is 347.22 g/mol (365.24 g/mol as the monohydrate, CAS 18422-05-4). It should not be confused with the 2′- and 3′-monophosphate isomers, which carry the phosphate on a different ribose hydroxyl, or with cyclic AMP (cAMP), in which the phosphate forms a ring between the 3′ and 5′ positions, or with ADP and ATP, which carry two and three phosphate groups.

Sigma-Aldrich’s reference grade is the monohydrate at ≥97% purity, stored at −20 °C; it dissolves in 1 M ammonium hydroxide at 50 mg/mL and in water once mild alkali is added.

Uses of Adenosine 5′-Monophosphate

AMP is the molecule through which cells read their energy state. When ATP is consumed and the AMP:ATP ratio rises, AMP binds AMPK and activates it, switching on catabolic pathways such as glucose uptake and fatty-acid oxidation and switching off energy-consuming biosynthesis. That makes AMP and its analogues central reagents in diabetes, obesity, cancer-metabolism and exercise-physiology research.

Biochemists also use AMP as a substrate and effector in enzyme studies (phosphorylase b, adenylate kinase, AMP deaminase), as a starting material for ADP, ATP and nucleotide-analogue synthesis, and as an HPLC standard for adenylate-energy-charge measurements.

Buying and Handling Considerations

Because AMP exists as the anhydrous acid, a hydrate and several salts with different molecular weights, state the form when you order and calculate molarity from the formula weight on the Certificate of Analysis. Protect the solid from moisture and store it at −20 °C in a tightly closed container, allowing it to warm to room temperature before opening. Nucleotides hydrolyse slowly in solution, so prepare solutions fresh or freeze small aliquots. Solutions of the free acid are acidic; dissolve with a little dilute base such as ammonium or sodium hydroxide and adjust the pH to the assay buffer.

Safety Information

Based on Sigma-Aldrich’s verified listing (A2252).

  • Pictogram / Hazard Statements: none assigned on the reference listing
  • Storage Class: 11 – Combustible solids | Flash Point: not applicable | Storage Temperature: −20°C

Handle with standard laboratory precautions: avoid generating dust, avoid contact with eyes and skin, wear gloves and safety glasses, and wash hands after use.

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FAQs: Adenosine Monophosphate

It is used in AMPK and other kinase assays, as a substrate or effector in enzymology, as a starting material for ADP, ATP and nucleotide-analogue synthesis, in NAD+ metabolism research and as an HPLC standard for adenine nucleotides.

AMP carries one phosphate group on the 5′-hydroxyl of adenosine, ADP carries two and ATP carries three. Cyclic AMP (cAMP) has its single phosphate closed into a ring between the 3′ and 5′ positions and acts as a second messenger.

AMP binds the regulatory γ-subunit of AMPK, which promotes phosphorylation of AMPK by upstream kinases and inhibits its dephosphorylation. Active AMPK then switches on energy-producing pathways and switches off energy-consuming ones.

The anhydrous free acid is C10H14N5O7P with a molecular weight of 347.22 g/mol. The monohydrate (CAS 18422-05-4) has a molecular weight of 365.24 g/mol, and salt forms differ again.

Dissolve it in water with a small amount of mild alkali, such as dilute ammonium or sodium hydroxide. Sigma-Aldrich lists water solubility on addition of mild alkali and reports 50 mg/mL in 1 M ammonium hydroxide as a clear, colourless solution.

Store the solid at −20 °C, tightly closed and protected from moisture. Make solutions fresh or freeze aliquots, because nucleotides hydrolyse slowly in solution.

Yes. SKU S3481 is supplied with a lot-specific Certificate of Analysis and Safety Data Sheet, and Sarchem Labs provides quotes from laboratory packs to bulk volumes.