23526-11-6

Basic information

• Product Name: 9-(2-deoxypentofuranosyl)-6-(methylsulfanyl)-9H-purine
• Synonyms: 9H-purine, 9-(2-deoxypentofuranosyl)-6-(methylthio)-
• CAS NO: 23526-11-6
• Molecular Formula: C₁₁H₁₄N₄O₃S
• Molecular Weight: 282.3189
• Mol File: 23526-11-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 592.3°C at 760 mmHg
• Flash Point: 312°C
• Density: 1.72g/cm³
• Vapor Pressure: 7.09E-15mmHg at 25°C
• Refractive Index: 1.79
• CAS DataBase Reference: 9-(2-deoxypentofuranosyl)-6-(methylsulfanyl)-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(2-deoxypentofuranosyl)-6-(methylsulfanyl)-9H-purine(23526-11-6)
• EPA Substance Registry System: 9-(2-deoxypentofuranosyl)-6-(methylsulfanyl)-9H-purine(23526-11-6)

Safety Data

• Hazardous Substances Data: 23526-11-6(Hazardous Substances Data)

Upstream product

• 51549-47-4 3',5'-di-O-acetyl-N₄-benzoyl-2'-deoxycytidine 
• 213769-47-2 N₄-benzoyl-2'-deoxycytidine 
• 145060-59-9 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(6-thioxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 2239-64-7 6-thiodeoxyinosine 
• 951-78-0 2'-deoxyuridine 
• 50-66-8 6-methylthiopurine 
• 76265-52-6 Acetic acid (2R,3S)-2-acetoxymethyl-5-(6-methylsulfanyl-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 342-69-8 6-methylmercaptopurine riboside 
• 2239-64-7 6-mercaptopurine-2’-deoxyribose 
• 74-88-4 methyl iodide 

Downstream Products

• 163882-50-6 (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methylsulfanyl-purin-9-yl)-tetrahydro-furan-3-ol 

Relevant articles and documents

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Methylation of mercaptopurine, thioguanine, and their nucleotide metabolites by heterologously expressed human thiopurine S-methyltransferase

Thiopurine S-methyltransferase (TPMT), a cytosolic enzyme that exhibits genetic polymorphism, catalyzes S-methylation of mercaptopurine (MP) and thioguanine (TG), yielding S-methylated nucleobases that are inactive, whereas S-methylated nucleotides of these thiopurines are cytotoxic. A yeast- based heterologous expression system was therefore used to characterize human TPMT-catalyzed methylation of MP, TG, and their principal nucleotide metabolites [thioinosine monophosphate (TIMP) and thioguanosine monophosphate (TGMP), respectively]. MP, TG, TIMP, and TGMP were all substrates for human TPMT, exhibiting similar Michaelis-Menten kinetic parameters (K(m), 10.6- 27.1 μM; V(max), 31-59 nmol/min/mg of TPMT). Consistent with these kinetic parameters, human leukemia cells (CEM) incubated for 24 hr with 10 μM MP or TG accumulated significantly higher (2.3-fold, p = 0.01) concentrations of methyl-TIMP after MP incubation than methyl-TGMP after TG incubation, due to the 2.7-fold higher concentration of TIMP after MP incubation, compared with TG nucleotides (TGN) after TG incubation. Moreover, intracellular accumulation of TGN was 2.5-fold greater after TG incubation than after MP incubation (p = 0.01). These data establish that MP, TG, and their principal nucleotide metabolites are comparable substrates for polymorphic TPMT, and they demonstrate significant differences in the accumulation of active TGN and methylated nucleotides when leukemia cells are treated with MP versus TG.

SYNTHESIS OF 2-DEOXY-β-D-RIBONUCLEOSIDES AND2,3-DIDEOXY.β-D-PENTOFURANOSIDES ON IMMOBILIZED BACTERIAL CELLS

Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs.All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N9-isomers in the purine and N1-isomers in the pyrimidine series.Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety.The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N7-nitrogen atom.On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives.Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed.The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-deoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-deoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.