2504-55-4

Basic information

• Product Name: 3'-AMINO-D-ADENOSINE
• Synonyms: 3'-AMINO-D-ADENOSINE;3'-AMINO-3'-DEOXY-D-ADENOSINE;3'-amino-3'-deoxyadenosine;3'-Deoxy-3'-aminoadenosine;Adenosine,3'-amino-3'-deoxy-
• CAS NO: 2504-55-4
• Molecular Formula: C₁₀H₁₄N₆O₃
• Molecular Weight: 282.25596
• Mol File: 2504-55-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 260-261 °C
• Boiling Point: 409.46°C (rough estimate)
• Flash Point: 351.5°C
• Appearance: /
• Density: 1.2946 (rough estimate)
• Refractive Index: 1.7000 (estimate)
• PKA: 13.27±0.70(Predicted)
• CAS DataBase Reference: 3'-AMINO-D-ADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-AMINO-D-ADENOSINE(2504-55-4)
• EPA Substance Registry System: 3'-AMINO-D-ADENOSINE(2504-55-4)

Safety Data

• Hazardous Substances Data: 2504-55-4(Hazardous Substances Data)

Usage

General Description

3'-Amino-D-adenosine, also known as 3'-amino-3'-deoxyadenosine, is a modified nucleoside that is derived from adenosine. It is an adenosine analog with a substituted amino group at the 3' position of the ribose ring. This modification can alter the properties of the nucleoside, affecting its reactivity and biological activity. 3'-Amino-D-adenosine has been studied for its potential therapeutic applications, particularly in the treatment of various diseases and conditions. It is also a useful tool in biochemical and pharmacological research for studying the effects of modified nucleosides on biological systems. Additionally, its potential use as a nucleoside transporter substrate in cancer therapy is also being investigated.

Upstream product

• 110154-50-2 3'-phthalimido-3'-deoxy-adenosine 
• 695183-20-1 3'-azido-3'-deoxy-2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-adenosine 
• 118525-25-0 9-[2',5'-bis-(O-tert-butyldimethylsilyl)-β-D-xylofuranosyl]-9H-adenine 
• 86734-95-4 9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 
• 65109-11-7 2',5'-bis-O-(tert-butyldimethylsilyl)adenosine 
• 889875-56-3 di-O-benzoyl-3-phthalimido-3-deoxy-β-D-ribofuranosyl chloride 
• 216976-72-6 Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 
• 216976-71-5 Benzoic acid (3R,4R,5S)-4-azido-2-methoxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester 
• 216976-70-4 Carbonic acid (3aR,5S,6R,6aR)-6-azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester methyl ester 
• 114861-16-4 Trifluoro-methanesulfonic acid (3aR,5R,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 216976-56-6 ((3aR,5S,6R,6aR)-6-Azido-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane 
• 114861-14-2 1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 23345-80-4 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 

Downstream Products

• 53-79-2 puromycin 
• 57183-05-8 tert-butyl [(S)-1-({(2S,3S,4R,5R)-5-[6-(dimethylamino)-9H-purin-9-yl]-4-hydroxy-2-(hydroxymethyl)tetrahydrofuran-3-yl}amino)-3-(4-methoxyphenyl)-1-oxopropan-2yl]carbamate 
• 58-60-6 3'-amino-3'-deoxy-N⁶,N⁶-dimethyladenosine 
• 168985-12-4 Toluene-4-sulfonic acid (2R,3R,4R,5S)-2-(6-amino-purin-9-yl)-4-tert-butoxycarbonylamino-5-(hydroxy-phosphonomethyl-phosphinoyloxymethyl)-tetrahydro-furan-3-yl ester 
• 168985-11-3 C₂₉H₃₄N₆O₉S₂ 
• 168985-13-5 Toluene-4-sulfonic acid (2R,3R,4R,5S)-4-amino-2-(6-amino-purin-9-yl)-5-(hydroxy-phosphonomethyl-phosphinoyloxymethyl)-tetrahydro-furan-3-yl ester 
• 168985-14-6 3'-Amido-3'-desoxy-2'-O-tosyladenosin-3',5'-cyclomethylenbis(phosphonat) 

Relevant articles and documents

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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.

An efficient synthesis of 3′-amino-3′-deoxyguanosine from guanosine

3′-Amino-3′-deoxyguanosine was synthesized from guanosine in eight steps and 58% overall yield. The 2′,3′-diol of 5′-O-[(tert-butyl)diphenylsilyl]-2-N-[(dimethylamino) methylidene]guanosine was reacted with α-acetoxyisobutyryl bromide and treated with 0.5N NH3 in MeOH to yield 9-[2′-O-acetyl-3′-bromo-5′-O-[(tertbutyl) diphenylsilyl]-3′-deoxy-β-D-xylofuranosyl]-2-N- [(dimethylamino)methylidene]guanine, which was reacted with benzyl isocyanate, NaH, and then 3.0N NaOH, and finally with Pd/C (10%) and HCO2NH4 in EtOH/AcOH to afford 3′-amino-3′-deoxyguanosine.