222736-08-5

Upstream product

• 211919-88-9 (5?'S)-N⁶-benzoyl-3?'-O-(tert-butyldimethylsilyl)-5?',8-cyclo-2?'-deoxyadenosine 
• 222736-07-4 C₂₄H₃₁N₅O₆SSi 

Downstream Products

• 222736-09-6 (5'R)-N₆-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine 
• 222736-10-9 (5'R)-N₆-benzoyl-5'-O-(4,4-dimethoxytrityl)-5',8-cyclo-2'-deoxyadenosine 

Relevant academic research and scientific papers

(5′R)-5′,8-Cyclo-2′-deoxyadenosine: NMR and DFT study of its influence on TPOcdA structure

Oxidatively generated damage to DNA frequently appears in the human genome as an effect of aerobic metabolism or as the result of exposure to exogenous oxidizing agents, such as ionizing radiation and solar light, a product of radiation. 5′,8-Purine cyclo

Synthesis and characterization of oligonucleotides containing 5',8- cyclopurine 2'-deoxyribonucleosides: (5'R)-5',8-cyclo-2'-deoxyadenosine, (5'S)-5',8-cyclo-2'-deoxyguanosine, and (5'R)-5',8-cyclo-2'-deoxyguanosine

Radiation-induced degradation of purine and pyrimidine nucleosides gave rise to carbon-bridged cyclocompounds. Such cyclonucleosides represent a class of tandem lesions in which modification of both the base and 2- deoxyribose has occurred. A solid-phase synthetic method was designed for the incorporation of both 5'R and 5'S diastereoisomers of 5',8-cyclopurine 2'- deoxyribonucleosides into oligodeoxynucleotides to facilitate the assessment of the biochemical and biophysical features of such lesions. We report the preparation of the phosphoramidite synthons of (5'R)-5',8-cyclo-2'- deoxyadenosine (2), (5'S)-5',8-cyclo-2'-deoxyguanosine (3), and (5'R)-5',8- cyclo-2'-deoxyguanosine (4). Fully protected compounds 10, 18, and 25 were then inserted into several oligonucleotides by automated procedures. Analysis of modified DNA oligomers 26-31 by electrospray mass spectrometry and enzymatic digestions with exo- and endonucleases confirmed the base compositions and the integrity of free radical-induced tandem lesions 2-4 that were chemically inserted.

Synthesis and characterization of oligodeoxynucleotides containing 5',8- cyclopurine-2'-deoxyribonucleosides

Oligodeoxynucleotides containing the two 5'R and 5'S diastereoisomers of 5',8-cyclo-2'-deoxyadenosine (CyclodAdo) and 5',8-cyclo-2'-deoxyguanosine (CyclodGuo) have been synthesized using the phosphoramidite chemistry. The structural assignment and a few b