4546-73-0

Upstream product

• 951-78-0 2'-deoxyuridine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 452-51-7 D-2-deoxyribose 
• 134-58-7 8-azaguanine 
• 961-07-9 2'-Deoxyguanosine 
• 152042-83-6 5-amino-3-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-7-methoxy-3H-1,2,3-triazolo<4,5-d>pyrimidine 
• 152042-88-1 5-amino-3-(2-deoxy-β-D-erythro-pentofuranosyl)-7-methoxy-3H-1,2,3-triazolo<4,5-d>pyrimidine 
• 37113-44-3 5,7-diamino-3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-1,2,3-triazolo<4,5-d>pyrimidine 

Downstream Products

• 160999-23-5 3-<2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-5-<<(dimethylamino)methylene>amino>-3,6-dihydro-7H-1,2,3-triazolo<4,5-d>pyrimidin-7-one 

Relevant academic research and scientific papers

Enzymatic synthesis of 2-deoxy-β-d-ribonucleosides of 8-azapurines and 8-aza-7-deazapurines

The enzymatic synthesis of 8-azapurine and 8-aza-7-deazapurine 2-deoxyribonucleosides has been studied. Two methods have been used: (i) transglycosylation employing 2-deoxyguanosine, 2-deoxycytidine, 2-deoxyuridine, and 2-deoxythymidine as 2-deoxy-d-ribofuranose donors and recombinant E. coli purine nucleoside phosphorylase (PNP) as biocatalyst, and (ii) one-pot synthesis from 2-deoxy-d-ribose and nucleobases employing recombinant E. coli ribokinase (RK), phosphopentomutase (PPM) and PNP as biocatalysts. Good substrate activity was observed for all bases studied except 2-amino-8-aza-6-chloro-7-deazapurine, which afforded the desired N9-nucleoside in moderate yield due to very low solubility of the base and partial replacement of C6-chloro atom of the base and formed nucleoside with a hydroxy group. The participation of Ser90 Oγ of E. coli PNP in the binding of 8-aza-7-deazapurines in the catalytic center of PNP followed by the formation of a productive complex and glycosidic bond is suggested. Georg Thieme Verlag Stuttgart · New York.

8-Aza-2′-deoxyguanosine: Base pairing, mismatch discrimination and nucleobase anion fluorescence sensing in single-stranded and duplex DNA

Oligodeoxyribonucleotides containing 8-aza-2′-deoxyguanosine 9 were synthesized and a new phosphoramidite 11, showing a high coupling yield in solid-phase synthesis, was prepared. Nucleoside 9 was found to be a perfect shape mimic of dG; it forms a strong

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.