227950-65-4

Upstream product

• 79-30-1 isobutyryl chloride 
• 198008-12-7 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate 
• 83-01-2 diphenylcarbamic chloride 
• 227950-62-1 7-(2-deoxy-β-D-erythro-pentofuranosyl)-1,7-dihydro-4-[(2-methylpropanoyl)amino]-2H-pyrrolo[2,3-d]pyrimidin-2-one 
• 103173-80-4 4-amino-7-(2-deoxy-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-2(3H)-one 
• 103173-80-4 4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo<2,3-d>pyrimidin-2-one 
• 104291-20-5 (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 

Downstream Products

• 227950-66-5 7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate 

Relevant academic research and scientific papers

The base-pairing properties of 7-deaza-2'-deoxyisoguanosine and 2'- deoxyisoguanosine in oligonucleotide duplexes with parallel and antiparallel chain orientation

Oligonucleotides with parallel (ps) or antiparallel (aps) chain orientation containing 7-deaza-2'-deoxyisoguanosine (1) or 2'- deoxyisoguanosine (2) were prepared. The phosphoramidite and phosphonate building blocks 3-6 were synthesized and used in solid-phase synthesis. The diphenylcarbamoyl (dpc) residue was used for the 2-oxo group protection and the isobutyryl (iBu=ib) residue for the amino function. Hybridization experiments were performed with oligonucleotides containing 7-deazaisoguanine or isoguanine. Regarding 7-deazapurine-containing oligonucleotides, the 7- deazaisoguanine cytosine base pair was the strongest in ps-duplexes, while that of 7-deazaisoguanine. 5-methylisocytosine was the most stable one in apsDNA. Ambiguous base pairing of 7-deazaisoguanine with cytosine, 5- methylisocytosine, thymine, and guanine was observed in the case of aps- duplexes, whereas in ps-duplexes, the ambiguity was extended to adenine. The 7-deazaisoguanine-containing duplexes showed almost identical base-pair stabilities as those containing isoguanine. According to this, various base- pair motifs are proposed. The 7-deaza-2'-deoxyisoguanosine was found to be an effective substitute of 2'-deoxyisoguanosine.

Oligonucleotides containing consecutive 2'-deoxy-isoguanosine residues: Synthesis, parallel duplex formation and identification of a d(T4iG4T4) tetraplex

Oligonucleotides containing consecutive 2'-deoxyisoguanosines were synthesized by using building blocks protected with a diphenylcarb-amoyl residue. Parallel duplexes were formed by iG(d)-dC base pairs and a tetraplex of d(T4iG4T4) was identified by ion exchange HPLC.

7-Deazaisoguanine quartets: Self-assembled oligonucleotides lacking the Hoogsteen motif

Oligonucleotides containing consecutive 7-deazaisoguanine residues form self-assembled quartets, indicating that the purine nitrogen-7 of isoguanine is not participating in the hydrogen bonding pattern.