The C-8-(2 `-deoxy-beta-D-ribofuranoside) of 7-deazaguanine: Synthesis and base pairing of oligonucleotides with unusually linked nucleobases

Autor(en): Seela, F
Debelak, H
Stichwörter: BUILDING-BLOCKS; Chemistry; Chemistry, Organic; DNA; DUPLEX STABILIZATION; GLYCOSYLATION; ISOGUANINE; NUCLEOSIDE; OLIGODEOXYRIBONUCLEOTIDES; PARALLEL; PYRROLO<2,3-D>PYRIMIDINES; SOLID-PHASE SYNTHESIS
Erscheinungsdatum: 2001
Herausgeber: AMER CHEMICAL SOC
Journal: JOURNAL OF ORGANIC CHEMISTRY
Volumen: 66
Ausgabe: 10
Startseite: 3303
Seitenende: 3312
Zusammenfassung: 
The 7-deazaguanine (2-aminopyrrolo [2,3-d]pyrimidin-4-one) C-8-(2'-deoxy-beta -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 (m(5)isoC(d)) in oligonucleotide duplexes with antiparallel chain orientation and with dC in parallel duplex DNA. Thus, the CB-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.
ISSN: 00223263
DOI: 10.1021/jo001498q

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