The C(8)-(2'-deoxy-beta-D-ribofuranoside) of 7-deazaguanine: synthesis and base pairing of oligonucleotides with unusually linked nucleobases.
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 C(8)-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.
Seela
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F
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany. frank.seela@uni-osnabrueck.de
Debelak
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H
D020029:Base Pairing; D002942:Circular Dichroism; D004247:DNA / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D003855:Deoxyribose; D004355:Drug Stability; D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry; D013329:Structure-Activity Relationship
D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D003855:Deoxyribose; D006147:Guanine; D004247:DNA; D003849:Deoxyguanosine; C066856:7-deazaguanine