222736-22-3

Upstream product

• 222736-26-7 (5'R)-N₂-isobutyryl-3'-O-(triisopropylsilyl)-5'-O-6-O-diacetyl-5',8-cyclo-2'-deoxyguanosine 
• 222736-20-1 (5'S)-N₂-isobutyryl-3'-O-(triisopropylsilyl)-5',8-cyclo-2'-deoxyguanosine 
• 222736-19-8 N₂-isobutyryl-3'-O-(triisopropylsilyl)-5',8-cyclo-2',5'-dideoxyguanosine 
• 222736-12-1 N₂-isobutyryl-5'-phenylthio-2',5'-dideoxyguanosine 
• 222736-13-2 N₂-isobutyryl-5',8-cyclo-2',5'-dideoxyguanosine 
• 13154-24-0 triisopropylsilyl chloride 
• 68892-42-2 N-isobutyryl-2'-deoxyguanosine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 222736-21-2 (5'R)-N₂-isobutyryl-3'-O-(triisopropylsilyl)-5',8-cyclo-2'-deoxyguanosine 

Downstream Products

• 222736-23-4 (5'R)-N₂-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-5',8-cyclo-2'-deoxyguanosine 

Relevant academic research and scientific papers

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.