34536-05-5

Upstream product

• 126754-82-3 7-<2'-Deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-(methylthio)-7H-imidazo<4,5-d>-1,2,3-triazine 
• 951-78-0 2'-deoxyuridine 
• 2308-56-7 2-azaadenine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 958-09-8 2'-deoxy-D-adenosine 
• 151229-13-9 1-(2-Deoxy-β-D-erythro-pentafuranosyl)-5-amino-4-(imidazol-2''-yl)imidazole 
• 261776-85-6 3-(2-Deoxy-β-D-erythro-pentafuranosyl)-1H-diimidazo[1,2-c:4',5'-e][1,2,3]triazine 
• 68498-25-9 3-(2-Deoxy-β-D-erythro-pentafuranosyl)-3H-imidazo[2,1-i]purine 

Downstream Products

• 56220-50-9 7-(2-Deoxy-β-D-erythro-pentafuranosyl)-7H-imidazo[4,5-d][1,2,3]triazin-4-one 
• 261776-88-9 7-[2-Deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-4-{[(di-n-butylamino)methylidene]amino}-7H-imidazo[4,5-d][1,2,3]triazine 

Relevant academic research and scientific papers

2-AZAPURINE COMPOUNDS AND THEIR USE

Within oligonucleotides 2-azapurine and especially 2-azaadenine bases form specifically base pairs with guanine. This base pair is of analogous stability as an adenine-thymine but less stable than a guanine-cytosine base pair. Therefore, the incorporation

2-aza-2′-deoxyadenosine: Synthesis, base-pairing selectivity, and stacking properties of oligonucleotides

2-Aza-2′-deoxyadenosine (2, z2Ad) is synthesized via its 1,N6-etheno derivative 7 and enzymatically deaminated to 2-aza-2′-deoxyinosine (3). Compound 2 is converted into the phosphoramidite building block 10b. This is empl

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.

Stereoselective Synthesis of 2-Azapurine 2'-Deoxy-β-D-ribonucleosides by Nucleobase-Anion Glycosylation

Nucleobase-anion glycosylation of 6-(methylthio)-2-azapurine (1) with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (2) yields the 2'-deoxy-β-D-ribofuranosides 3-5 stereoselectively.The distribution of regioisomers is as follows: N-9 (32percent); N-2 (30percent), and N-7 (7percent) together with a minor amount of an unidentified labile glycosylation product.The anomeric configuration and the site of glycosylation have been assigned on the basis of the 1H-NOE difference spectral data in combination with gated-decoupled 13C-NMR and selective INEPT spectroscopy.The regioisomeric 6-methylthio nucleosides have been converted into 6-substituted derivatives of biological interest including 2'-deoxy-2-azaadenosine (8).Compound 8 is a substrate of adenosine deaminase.