Oligonucleotides containing consecutive 2'-deoxyisoguanosine residues: Synthesis, duplexes with parallel chain orientation, and aggregation
Autor(en): | Seela, F Wei, CF |
Stichwörter: | ANALOGS; BASE-PAIR; Chemistry; Chemistry, Multidisciplinary; ENZYMATIC INCORPORATION; ISOGUANOSINE; NUCLEOSIDES; OLIGODEOXYRIBONUCLEOTIDES; OLIGORIBONUCLEOTIDES; PROTECTING GROUPS; RNA | Erscheinungsdatum: | 1997 | Herausgeber: | NEW SWISS CHEMICAL SOC | Enthalten in: | HELVETICA CHIMICA ACTA | Band: | 80 | Ausgabe: | 1 | Startseite: | 73 | Seitenende: | 85 | Zusammenfassung: | The 2'-deoxyisoguanosine phosphonates 3a and 4a and the phosphoramidites 3b and 4b were prepared as building blocks for solid-phase oligonucleotide synthesis. The diphenylcarbamoyl (dpc) residue was introduced as Zero protecting group which stabilizes the N-glycosylic bond against hydrolysis and prevents the molecule from side reactions. The dpc-protected building blocks 4a,b were employed in solid-phase synthesis and were found to be much more efficient than the unprotected compounds 3a,b. Oligonucleotides with alternating (11) or consecutive isoguanine residues (13-15) were synthesized. They form duplexes with parallel chain orientation. The aggregate d(T-4-iG(4)-T-4) (15) containing four consecutive 2'-deoxyisoguanosine is shown to be a tetramer similar to that of d(T-4-G(4)-T-4). |
ISSN: | 0018019X | DOI: | 10.1002/hlca.19970800107 |
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geprüft am 06.06.2024