56973-12-7

Basic information

• Product Name: 8-methyladenosine
• Synonyms: 8-methyladenosine
• CAS NO: 56973-12-7
• Molecular Formula: C₁₁H₁₅N₅O₄
• Molecular Weight: 281.27
• Mol File: 56973-12-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 688.6°Cat760mmHg
• Flash Point: 370.2°C
• Appearance: /
• Density: 1.96g/cm³
• Vapor Pressure: 6.59E-20mmHg at 25°C
• Refractive Index: 1.856
• CAS DataBase Reference: 8-methyladenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-methyladenosine(56973-12-7)
• EPA Substance Registry System: 8-methyladenosine(56973-12-7)

Safety Data

• Hazardous Substances Data: 56973-12-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H15N5O4/c1-4-15-6-9(12)13-3-14-10(6)16(4)11-8(19)7(18)5(2-17)20-11/h3,5,7-8,11,17-19H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1

Upstream product

• 110526-63-1 2',3',5'-tris-O-(tert-butyldimethylsilyl)-8-methyladenosine 
• 65627-13-6 2',3'-O-isopropylidene-8-methyladenosine 
• 75-24-1 trimethylaluminum 
• 2946-39-6 8-bromoadenosine 
• 594-27-4 tetramethylstannane 
• 107-71-1 tert-butyl peroxyacetate 
• 58-61-7 adenosine 
• 64911-28-0 O^2'_,O3'_,O5'-tris-(tert-butyl-dimethyl-silanyl)-adenosine 
• 69359-30-4 5'-O-acetyl-8-ethoxycarbonylmethyl-2',3'-O-isopropylideneadenosine 
• 69359-29-1 5'-O-acetyl-2',3'-O-isopropylidene-8-methylsulfonyladenosine 

Downstream Products

• 68045-12-5 8-methyladenosine 5'-monophosphate 

Relevant articles and documents

Direct C-8 lithiation of naturally-occurring purine nucleosides. A simple method for the synthesis of 8-carbon-substituted purine nucleosides

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Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: A C2′ endo/syn "southern" ribose conformation underlies activity at the sea urchin cADPR receptor

Novel 8-substituted base and sugar-modified analogues of the Ca 2+ mobilizing second messenger cyclic adenosine 5′-diphosphate ribose (cADPR) were synthesized using a chemoenzymatic approach and evaluated for activity in sea urchin egg homogenate (SUH) and in Jurkat T-lymphocytes; conformational analysis investigated by 1H NMR spectroscopy revealed that a C2′ endo/syn conformation of the "southern" ribose is crucial for agonist or antagonist activity at the SUH-, but not at the T cell-cADPR receptor.

New insights into the design of inhibitors of human S-adenosylmethionine decarboxylase: studies of adenine C8 substitution in structural analogues of S-adenosylmethionine

S-Adenosylmethionine decarboxylase (AdoMetDC) is a critical enzyme in the polyamine biosynthetic pathway and depends on a pyruvoyl group for the decarboxylation process. The crystal structures of the enzyme with various inhibitors at the active site have shown that the adenine base of the ligands adopts an unusual syn conformation when bound to the enzyme. To determine whether compounds that favor the syn conformation in solution would be more potent AdoMetDC inhibitors, several series of AdoMet substrate analogues with a variety of substituents at the 8-position of adenine were synthesized and analyzed for their ability to inhibit hAdoMetDC. The biochemical analysis indicated that an 8-methyl substituent resulted in more potent inhibitors, yet most other 8-substitutions provided no benefit over the parent compound. To understand these results, we used computational modeling and X-ray crystallography to study C8-substituted adenine analogues bound in the active site.

PURINE NUCLEOTIDE DERIVATIVES

This invention provides novel 8-carbyl substituted cAMPS and a novel procedures for the preparation of 8-Br-cAMP, a key starting material.