Adenosine 5'-monophosphate monohydrate Chemical Properties

Melting point:

183-188 °C (dec.)(lit.)

alpha 

-48 º (c=2% in 2% NaOH)

FEMA 

4224 | ADENOSINE MONOPHOSPHATE; MONOSODIUM, OR DISODIUM ADENYLATE

storage temp. 

-20°C

solubility 

H₂O: with addition of mild alkalisoluble

form 

Solid

color 

White to Off-White

Merck 

14,158

BRN 

5205540

CAS DataBase Reference

18422-05-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

AU7480500

F 

8-10-21

TSCA 

Yes

HS Code 

2934999090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Adenosine 5'-monophosphate monohydrate Usage And Synthesis

Pharmacodynamics

Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP is used as a dietary supplement to boost immune activity, and is also used as a substitute sweetener to aid in the maintenance of a low-calorie diet.

Description

Adenosine 5'-monophosphate monohydrate is an adenosine A1 receptor agonist. Adenosine 5'-monophosphate monohydrate has significant antiviral activity against HSV-1 and HSV-2. It plays an important role in various biochemical pathways such as energy metabolism, gene expression and signal transduction.

Chemical Properties

White crystalline powder

Uses

Nutrient;Ca++ channel block

Uses

Adenosine 5′-monophosphate (5′AMP) is suitable for use as

• a reagent in the synthesis of adenosine-5′-phosphoimidazolide
• an activator of phosphorylase b in the polymerization reaction for the synthesis of branched polysaccharides
• an inhibitor of endogenous NMN adenylyltransferase (NMNAT) activity that converts NMN to NAD⁺

Definition

ChEBI: Adenosine 5'-monophosphate monohydrate is a purine ribonucleoside monophosphate.

Biochem/physiol Actions

Adenosine 5′-monophosphate (5′-AMP) has many uses in nature. 5′-AMP is an activator of a class of protein kinases known as AMP-activated protein kinase (AMPK). AMP inhibits dephosphorylation of AMPK and promotes phosphorylation of AMPK by upstream kinases.

Purification Methods

The acid has been recrystallised from H2O (fine needles) and is freely soluble in boiling H2O. It crystallises also from H2O on addition of acetone. Alternatively purify it by chromatography on Dowex 1 (in formate form), eluting with 0.25M formic acid. It is then adsorbed onto charcoal (which had been boiled for 15minutes with M HCl, washed free of chloride and dried at 100o) and recovered by stirring three times with isoamyl alcohol/H2O (1:9 v/v). The aqueous layer from the combined extracts is evaporated to dryness under reduced pressure, and the product is crystallised twice from hot H2O. [Morrison & Doherty Biochem J 79 433 1961]. It has max 259nm ( 15,400) in H2O at pH 7.0. [Alberty et al. J Biol Chem 193 425 1951, Martell & Schwarzenbach Helv Chim Acta 39 653 1956]. The acridinium salt has m 208o [Baddiley & Todd J Chem Soc 648 1947,
Pettit Synthetic Nucleotides, van Nostrand-Reinhold, NY, Vol 1 252 1972, NMR: Sarma et al. J Am Chem Soc 96 7337 1974, Norton et al. J Am Chem Soc 98 1007 1976, IR of diNa salt: Miles Biochem Biophys Acta 27 324 1958]. [Beilstein 26 III/IV 3615.]

Adenosine 5'-monophosphate monohydrate(18422-05-4)Related Product Information

• MELIBIOSE
• 2-Amino-2-methyl-1-propanol
• Cyclic AMP
• Adenosine
• Adenosine 5'-monophosphate
• ADP
• Adenosine5'-(tetrahydrogen triphosphate), disodiuM salt, trihydrate (9CI)
• ADENOSINE 5'-TRIPHOSPHATASE
• Vidarabine monophosphate
• ADENOSINE-5'-MONOPHOSPHATE DISODIUM SALT
• ATP disodium salt
• ADENOSINE 5'-DIPHOSPHATE SODIUM SALT
• ADENOSINE 5'-TRIPHOSPHATE DISODIUM SAL&
• Adenosine 3',5'-cyclic monophosphate sodium salt
• NADP sodium salt
• Nadph tetrasodium salt
• FLAVIN ADENINE DINUCLEOTIDE
• NAD+