N-7-DNA: Base-pairing properties of N-7-(2 `-deoxy-beta-D-erythro-pentofuranosyl)-substituted adenine, hypoxanthine, and guanine in duplexes with parallel chain orientation

Autor(en): Seela, F
Leonard, P
Stichwörter: BUILDING-BLOCKS; Chemistry; Chemistry, Multidisciplinary; DEOXYINOSINE; GLYCOSYLATION; N-7-(2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSYL)GUANINE N(7)G(D); OLIGODEOXYRIBONUCLEOTIDES; OLIGONUCLEOTIDES; RECOGNITION; SOLID-PHASE SYNTHESIS; STABILITY; TRIPLE-HELIX FORMATION
Erscheinungsdatum: 1998
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 81
Ausgabe: 12
Startseite: 2244
Seitenende: 2263
Zusammenfassung: 
Oligonucleotides containing N-7-(2'-deoxy-beta-D-erythro-pentofuranosyl)adenine (1),-hypoxanthine (2), and -guanine (3) were synthesized on solid-phase using phosphonate and phosphoramidite chemistry. As part of the synthesis of compound 2. the nucleobase-anion glycosylation of various 6-alkoxypurines with 2-droxy-3,5-di-O-(4-toluoyl)-alpha-D-erythro-pentofuranosyl chloride (5) was investigated. The duplex stability of oligonucleotides containing N-7-glycosylated purines opposite to regular pyrimidines was determined, and thermodynamic data were calculated from melting profiles. Oligodeoxyribonucleotide duplexes containing N-7-glycosylated adenine T-d or N-7-glycosylated guanine Cd base pairs are more stable in the case of parallel strand orientation than in the case of antiparallel chains.
ISSN: 0018019X

Show full item record

Page view(s)

1
Last Week
0
Last month
1
checked on Feb 22, 2024

Google ScholarTM

Check