Adenosine 5'-monophosphate monohydrate

Chemical properties

White crystalline powder

The Uses of Adenosine 5'-monophosphate monohydrate

Nutrient;Ca++ channel block

The Uses of Adenosine 5'-monophosphate monohydrate

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.]