341981-84-8Relevant academic research and scientific papers
The C8-(2′-deoxy-β-d-ribofuranoside) of 7-deazaguanine: Synthesis and base pairing of oligonucleotides with unusually linked nucleobases
Seela,Debelak
, p. 3303 - 3312 (2007/10/03)
The 7-deazaguanine (2-aminopyrrolo[2,3-d]pyrimidin-4-one) C8-(2′-deoxy-β-D-ribofuranoside) (6b), which possesses an unusual glycosylation site, was synthesized and incorporated in oligonucleotides. The oligonucleotides were prepared by solid-phase synthesis using phosphoramidite chemistry and were hybridized to form duplex DNA. Compound 6b is able to form base pairs with 2′-deoxy-5-methylisocytidine (m5isoCd) in oligonucleotide duplexes with antiparallel chain orientation and with dC in parallel duplex DNA. Thus, the C8-nucleoside 6b shows a similar base recognition as 2′-deoxyisoguanosine but not as 2′-deoxyguanosine. This indicates that the nucleic acid recognition not only depends on the donor-acceptor pattern of the nucleobase but is influenced by the glycosylation site. Base pairs of compound 6b formed with canonical and modified nucleosides are proposed.
8-Aza-7-deazaadenine and 7-deazaguanine: Synthesis and properties of nucleosides and oligonucleotides with nucleobases linked at position-8
Seela,Debelak
, p. 577 - 585 (2007/10/03)
The 8-aza-7-deazaadenine (pyrazolo[3,4-d]pyrimidin-4-amine) N8-(2′-deoxyribonucleoside) (2) and the 7-deazaguanine (pyrrolo[3,4-d]pyrimidine-2-amin-(3H)-4-one) C8-(2′-deoxyribonucleoside) (4) were synthesized and incorporated in olig
