8-aza-7-deazaadenine and 7-deazaguanine: Synthesis and properties of nucleosides and oligonucleotides with nucleobases linked at position-8

Autor(en): Seela, F
Debelak, H
Stichwörter: Biochemistry & Molecular Biology; BUILDING-BLOCKS; DNA; NMR; SOLID-PHASE SYNTHESIS
Erscheinungsdatum: 2001
Herausgeber: TAYLOR & FRANCIS INC
Journal: NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Volumen: 20
Ausgabe: 4-7
Startseite: 577
Seitenende: 585
Zusammenfassung: 
The 8-aza-7-deazaadenine (pyrazolo[3,4-d]pyrimidin-4-amine) N-8-(2'-deoxyribonucleoside) (2) and the 7-deazaguanine (pyrrolo[3,4-d]pyrimidine-2-amin-(3H)-4-one) C-8-(2'-deoxyribonucleoside) (4) were synthesized and incorporated in oligonucleotides employing phosphoramidite chemistry. Oligonucleotides carrying compound 2 are able to form base pairs with the four canonical DNA constituents without significant structural discrimination. The nucleoside 4 was obtained from the corresponding ribonucleoside by deoxygenation. Oligonucleotides containing compound 4 showed similar base pairing properties as those with 2'-deoxyisoguanosine.
Beschreibung: 
14th International Roundtable on Nucleosides, Nucleotides and their Biological Applications, SAN FRANCISCO, CA, SEP 10-14, 2000
ISSN: 15257770
DOI: 10.1081/NCN-100002334

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