3868-33-5

Basic information

• Product Name: 8-AMINOADENOSINE
• Synonyms: 8-AMINOADENOSINE;8-Amino-D-adenosine;NSC 90394;9H-Purine, 6,8-diamino-9-.beta.-D-ribofuranosyl-;6,8-Diamino-9-beta-D-ribofuranosyl-9H-purine;6,8-DiaMino-9-β-D-ribofuranosyl- 9H-purine;8-NH2-Ado;8-Amionadenosine
• CAS NO: 3868-33-5
• Molecular Formula: C10H14N6O4
• Molecular Weight: 282.26
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Amines;Heterocycles
• Mol File: 3868-33-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 180-185°C dec.
• Boiling Point: 747.1 °C at 760 mmHg
• Flash Point: 405.6 °C
• Appearance: white to beige/
• Density: 2.25
• Refractive Index: 1.986
• Storage Temp.: -20?C Freezer
• Solubility: H2O: soluble2mg/mL, clear (warmed)
• PKA: 13.07±0.70(Predicted)
• CAS DataBase Reference: 8-AMINOADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-AMINOADENOSINE(3868-33-5)
• EPA Substance Registry System: 8-AMINOADENOSINE(3868-33-5)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 3868-33-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

The purine nucleoside analog

InChI:InChI=1/C10H14N6O4/c11-7-4-8(14-2-13-7)16(10(12)15-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,15)(H2,11,13,14)/t3-,5+,6?,9-/m1/s1

Upstream product

• 4372-67-2 8-azidoadenosine 
• 2946-39-6 8-bromoadenosine 
• 67-56-1 methanol 
• 23205-66-5 O^2'_,O3'_,O5'5'-triacetyl-8-fluoro-adenosine 
• 288-32-4 1H-imidazole 
• 68144-29-6 8-azido-2',3'-O-isopropylideneadenosine 
• 13089-45-7 8-bromo-2',3'-O-isopropylene adenosine 
• 362-75-4 2',3'-isopropylidene adenosine 

Relevant articles and documents

8-Substituted, syn-Configured Adenosine Derivatives as Potential Inhibitors of the Enzyme IspE from the Non-Mevalonate Pathway of Isoprenoid Biosynthesis

The enzymes of the non-mevalonate pathway for isoprenoid biosynthesis are attractive targets for drugs against various diseases, including malaria. We describe herein the structure-based design, synthesis, conformational analysis, and biological evaluation of several 8-brominated or 8-aminated adenosine derivatives with different substituents at C(5′), targeting the ATP-adenine binding site of the IspE protein from the non-mevalonate pathway. An exhaustive conformational analysis of the adenosine derivatives both in solution and in the solid state confirmed the desired syn orientation of the adenine moiety. Despite this favorable pre-organization for binding to the cofactor pocket, biological evaluation of the inhibitors showed only a very modest inhibitory activity.

Radical reactions in aqueous medium using (Me3Si)3SiH

(Chemical Equation Presented) (Me3Si)3SiH was used as a successful reagent in a variety of radical-based transformations in water. The system comprising substrate, silane, and initiator (ACCN) mixed in aqueous medium at 100°C worked well for both hydrophilic and hydrophobic substrates, with the only variation that an amphiphilic thiol was also needed in case of the water-soluble compounds.

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.