4372-67-2

Basic information

• Product Name: 8-AZIDOADENOSINE
• Synonyms: (2R,3R,4S,5R)-2-(6-amino-8-azidopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;(2R,3R,4S,5R)-2-(6-amino-8-azido-purin-9-yl)-5-methylol-tetrahydrofuran-3,4-diol;(2R,3R,4S,5R)-2-(6-azanyl-8-azido-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;(2R,3R,4S,5R)-2-(6-amino-8-azido-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol;8-azido-adenosin;8-N3-ADO;8-AZIDOADENOSINE;8-AZIDO-D-ADENOSINE
• CAS NO: 4372-67-2
• Molecular Formula: C₁₀H₁₂N₈O₄
• Molecular Weight: 308.25
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides
• Mol File: 4372-67-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: >200?C (dec.)
• Appearance: Pink solid
• Storage Temp.: Amber Vial, Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Sparingly), Methanol (Slightly), Water (Slightly)
• Stability: Light Sensitive, Moisture Sensitive
• CAS DataBase Reference: 8-AZIDOADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-AZIDOADENOSINE(4372-67-2)
• EPA Substance Registry System: 8-AZIDOADENOSINE(4372-67-2)

Safety Data

• Hazardous Substances Data: 4372-67-2(Hazardous Substances Data)

Usage

Chemical Properties

Pink Solid

Uses

One compound, 8-azidoadenosine, inhibits CDP reduction in cytosolic extracts from cancer cells. 8-Azidoadenosine is an adenosine analogue conjugated with an azido group which can be used for oligonucleotide labelling. The azido group reacts with a terminal alkyne via a click reaction, forming the labelled nucleotide containing a triazole linker.

InChI:InChI=1/C10H12N8O4/c11-7-4-8(14-2-13-7)18(10(15-4)16-17-12)9-6(21)5(20)3(1-19)22-9/h2-3,5-6,9,19-21H,1H2,(H2,11,13,14)/t3-,5-,6-,9-/m1/s1

Upstream product

• 3868-34-6 8-hydrazinoadenosine 
• 2946-39-6 8-bromoadenosine 
• 58-61-7 adenosine 

Downstream Products

• 60731-47-7 8-azidoadenosine-5'-monophosphate 
• 1423158-32-0 8-amino-2-hydroxyadenosine 
• 1423158-34-2 C₆H₁₃N₃O₄ 
• 1423158-33-1 8-amino-2-imidazolyladenosine 
• 3868-33-5 8-aminoadenosine 
• 92001-68-8 8-azido-1-benzyladenine 
• 126709-23-7 8-azido-N⁶,2'-O,3'-O-tribenzoyl-5'-O-(monomethoxytrityl)adenosine 
• 126709-22-6 8-azido-N⁶-benzoyl-5'-O-(monomethoxytrityl)adenosine 
• 126709-24-8 8-azido-N⁶,2'-O,3'-O-tribenzoyladenosine 
• 126709-21-5 8-azido-N⁶-benzoyladenosine 
• 126709-20-4 8-azido-N⁶,N⁶,2'-O,3'-O,5'-O-pentabenzoyladenosine 
• 79270-98-7 8-Azidoadenine 

Relevant articles and documents

Immunophotoaffinity labeling of binders of 1-methyladenine, the oocyte maturation-inducing hormone of starfish

Starfish oocytes are arrested at the prophase stage of the first meiotic division in the ovary and resume meiosis by the stimulus of 1-methyladenine (1-MeAde), the oocyte maturation-inducing hormone of starfish. Putative 1-MeAde receptors on the oocyte surface have been suggested, but not yet been biochemically characterized. Immunophotoaffinity labeling, i.e., photoaffinity labeling combined with immunochemical detection, was attempted to detect unknown 1-MeAde binders including putative maturation-inducing hormone receptors in starfish oocytes. When the oocyte crude membrane fraction or its Triton X-100/EDTA extract was incubated with N6-[6-(5-azido-2-nitrobenzoyl)aminohexyl]carboxamidomethyl-1-methyladenine and then photo-irradiated, followed by western blotting with antibody that was raised against a 1-MeAde hapten, a single band with Mr of 47.5?K was detected. The band was lost when extract was heated at 100?°C. A similar 47.5?K band was detected in the crude membrane fraction of testis as well. Upon labeling with whole cells, this band was detected in immature and maturing oocytes, but only faintly in mature oocytes. As judged from these results, this 1-MeAde binder might be a possible candidate of the starfish maturation-inducing hormone receptors.

Convenient synthesis of 8-amino-2′-deoxyadenosine

We studied the behaviour of 8-azido-2′-deoxyadenosine and 8-bromo-2′-deoxyadenosine in aqueous solutions of ammonia and primary and secondary amines. Unexpectedly, 8-Azido-2′-deoxyadenosine is converted to 8-amino-2′-deoxyadenosine in excellent yields. The use of this reaction for the preparation of 8-aminoadenine derivatives needed for the preparation of oligonucleotides carrying 8-aminoadenine is discussed.