Oligonucleotides containing 7-deazaadenines: The influence of the 7-substituent chain length and charge on the duplex stability

Autor(en): Seela, F
Zulauf, M
Stichwörter: BUILDING-BLOCKS; CELLS; Chemistry; Chemistry, Multidisciplinary; CHIMERIC OLIGODEOXYNUCLEOTIDE ANALOGS; DELIVERY; DEOXYRIBONUCLEIC-ACID; DNA; OLIGODEOXYRIBONUCLEOTIDES; SEQUENCE
Erscheinungsdatum: 1999
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 82
Ausgabe: 11
Startseite: 1878
Seitenende: 1898
Zusammenfassung: 
Oligonucleotides carrying alkynyl and aminoalkynyl chains at the position 7 of 7-deazaadenine are synthesized. and the chain lengths as well as the bulkiness of the substituents are varied. The corresponding nucleosides 1a-f are prepared from 7-deaza-2'-deoxy-7-iodoadenosine and the particular alkynes by the Pd-0-catalyzed cross-coupling reaction. The nucleosides are converted to the phosphoramidites 2a-f, with are used in solid-phase oligonucleotide synthesis. The stability of the duplexes is determined by the T-m values and the thermodynamic data. Compared to adenine or the unsubstituted 7-deazaadenine, the incorporation of a 7-ethynyl chain in a 7-deazaadenine moiety increases the duplex stability significantly, while a dodecynyl residue or a bulky steroid moiety leads to a duplex destabilization. A 3-aminoprop-1-ynyl residue (see 1g) or a 5-aminopent-1-ynyl residue (see 1h), which are charged under neutral conditions, lead to zwitterionic DNA. A high density of charged residues as found in homomers impairs duplex formation. most probably by counter-ion condensation.
ISSN: 0018019X
DOI: 10.1002/(SICI)1522-2675(19991110)82:11<1878::AID-HLCA1878>3.0.CO;2-W

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