2096-10-8 Usage
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
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.https://doi.org/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.http://dx.doi.org/10.1080/15257770500544529
Check Digit Verification of cas no
The CAS Registry Mumber 2096-10-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,9 and 6 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2096-10:
(6*2)+(5*0)+(4*9)+(3*6)+(2*1)+(1*0)=68
68 % 10 = 8
So 2096-10-8 is a valid CAS Registry Number.
2096-10-8Relevant articles and documents
High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries
Bookser, Brett C.,Raffaele, Nicholas B.
, p. 173 - 179 (2007/10/03)
The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.
