Description
2-Aminoadenosine is a known analogue of adenosine that engages in three hydrogen bonds of the W-C type, adding considerable stability to the double helix.
Chemical Properties
White Powder
Uses
2-Aminoadenosine is a nucleoside analog as inhibitor or substrate of adenosine kinase from M. tuberculosis. It is also used to synthesize 2′-O-methyl and 3′-O-methyl Guanosine.
Definition
ChEBI: 2-Aminoadenosine is a purine nucleoside.
Synthesis
The synthesis of 2-aminoadenosine (2-AA): Assays were performed in 5 and 10% of aprotic dipolar co-solvents, at 60°C, twelve units/ml cell lysate were added to 150 ml of a solution kept thermostatically at 60 °C, and having the following composition of substrate solutions: 15mM Uridine/2 ' -Deoxyuridine,5 mM 2,6-Diaminopurine, and 30 mM potassium phosphate buffer, pH 7. After 5 hours, the reaction mixture was filtered by centrifugation at 2000 x g for 30 min, at 4°C, through an Amicon ultra-4 Centrifugal Filter Devices (Millipore, Bedford, MA) with a 3000-Da cutoff, and the filtrate was recovered.
References
Pyrazolo[3,4-d]pyrimidine ribonucleosides related to 2-aminoadenosine and isoguanosine: synthesis, deamination and tautomerism. DOI:
10.1039/B708736E An Efficient Process for Synthesis of 2′-O-methyl and 3′-O-methyl Guanosine from 2-aminoadenosine Using Diazomethane and the Catalyst Stannous Chloride. DOI:
10.1080/15257770500544529
