10414-81-0

Basic information

• Product Name: 2'-Amino-2'-deoxyadenosine
• Synonyms: 2'-AMINO-D-ADENOSINE;2'-Amino-2'-deoxy-D-adenosine;(2R,3S,4R,5R)-4-Amino-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol;2'-Amino-2'-deoxyadenosine;9-(2-Amino-2-deoxy-β-D-ribofuranosyl)-adenine;Adenosine, 2'-amino,-2'-deoxy;Jci-2172;Nsc324326
• CAS NO: 10414-81-0
• Molecular Formula: C10H14N6O3
• Molecular Weight: 266.26
• Mol File: 10414-81-0.mol

Chemical Properties

• Melting Point: 190-191 °C
• Boiling Point: 657.6 °C at 760 mmHg
• Flash Point: 351.5 °C
• Appearance: White to Off-white/Powder
• Density: 2.08 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Soluble in DMSO.
• PKA: 13.42±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2'-Amino-2'-deoxyadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Amino-2'-deoxyadenosine(10414-81-0)
• EPA Substance Registry System: 2'-Amino-2'-deoxyadenosine(10414-81-0)

Safety Data

• Hazardous Substances Data: 10414-81-0(Hazardous Substances Data)

Usage

Uses

2'-AdA can be used as starting material for the synthesis of 2'-amino nucleotides.

Upstream product

• 76727-55-4 9-(2-acetamido-2-deoxy-3,5-diacetyl-β-D-ribofuranosyl)-6-chloropurine 
• 66224-66-6 adenine 
• 26889-39-4 1-(2-amino-2-deoxy-β-D-ribofuranosyl)uracil 
• 88121-25-9 9-[3′,5′-O-(1,1,3,3-tetraisopropyldisiloxyl)-2′-O-trifluormethylsulfonyl-β-D-arabinofuranosyl]adenine 
• 401812-92-8 4-tert-butyl-N-{9-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-9H-purin-6-yl}-benzamide 
• 75763-51-8 2'-amino-2'-deoxyinosine 
• 129835-14-9 (2R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-3,3(2H)-diol 
• 82870-42-6 9-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>adenine 
• 118525-22-7 (2R,3S,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-3-yl trifluoromethanesulfonate 
• 695183-22-3 9-((2R,3R,4S,5R)-3-azido-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-9H-purin-6-amine 
• 58-61-7 adenosine 
• 69504-03-6 3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine 
• 76742-34-2 9-(2-acetamido-2-deoxy-3,5-diacetyl-β-D-ribofuranosyl)hypoxanthine 
• 184296-98-8 (2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-ol 

Downstream Products

• 75763-51-8 2'-amino-2'-deoxyinosine 
• 1208347-10-7 (2R,3R,4S,5R)-N-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl-[2-(methylamino)]benzamide 

Relevant articles and documents

Synthesis of non-hydrolyzable substrate analogs for Asp-tRNAAsn/Glu-tRNAGln amidotransferase

Non-hydrolyzable substrate analogs for tRNA-dependent amidotransferase, 2′- or 3′-aspartyl or -glutamyl adenosine, were synthesized from adenosine without protection of the adenine base. The hydroxyl groups of adenosine were selectively protected, followed by a series of oxidation/reductions to alter the stereochemistry. DFT calculations revealed the driving forces for the ketone hydrate formation at C-2′, but not the C-3′ carbon during the oxidation step. Subsequently, triflation and azide replacement yielded azidoadenosines, which were coupled to protected amino acids after deprotection and reduction. After global deprotection, the target substrate analogs were obtained in 2-14% overall yields from adenosine.

Scaleable and efficient synthesis of 2'-deoxy-2'-N-phthaloyl nucleoside phosphoramidites for oligonucleotide synthesis.

2'-Deoxy-2'-N-phthaloyl nucleosides were prepared from arabino nucleosides by triflate displacement with phthalimide in the presence of DBU. The corresponding phosphoramidites suitable for automated oligonucleotide synthesis were also synthesized. The scalability of described procedures was demonstrated on a 100-g scale preparation of 2'-deoxy-2'-amino-C phosphoramidite.

Nucleic acid related compounds. 91. Biomimetic reactions are in harmony with loss of 2'-substituents as free radicals (not anions) during mechanism-based inactivation of ribonucleotide reductases. Differential interactions of azide, halogen, and alkylthio

The initial step in the mechanism-based inactivation of ribonucleotide reductases by 2'-chloro-2'deoxynucleotides is abstraction of H3' by a proximal free radical on the enzyme. The C3' radical is postulated to undergo spontaneous loss of chloride, and th

Microbial Synthesis of Purine 2'-Amino-2'-deoxyribosides

The microbial synthesis of some purine 2'-amino-2'-deoxyribonucleosides from purine bases and 2'-amino-2'-deoxyuridine is described.Various bacteria, especially Erwinia herbicola, Salmonella schottmuelleri, Enterobacter aerogenes and Escherichia coli, were able to transfer the aminoribosyl moiety of 2'-amino-2'-deoxyuridine to purine bases (transaminoribosylation) in the presence of inorganic phosphate.The optimum conditions for the reaction were pH 7.0 and 63 deg C.No reaction was observed in the abscence of inorganioc phosphate and the optimum concentration of it was around 30 mM.Adenine, guanine, 2-chlorohypoxanthine and hypoxanthine were transformed to the corresponding 2'-amino-2'-deoxyribonucleosides by the catalytic activity of the wet cell paste of Enterobacter aerogenes AJ 11125.The enzymatically synthesized purine 2'-amino-2'-deoyxyribonucleosides were isolated and identified by physicochemical means. 2'-Amino-2'-deoxyadenosine strongly inhibited the growth of Hela cells in theis tissue culture, and the ED50 was 2.5 μg/ml.