7-deazaadenine-DNA: Bulky 7-iodo substituents or hydrophobic 7-hexynyl chains are well accommodated in the major groove of oligonucleotide duplexes

Autor(en): Seela, F
Zulauf, M
Stichwörter: 2'-DEOXYTUBERCIDIN; 7-DEAZA-2'-DEOXYADENOSINE; 7-IODO-2'-DEOXYTUBERCIDIN; B-DNA; BASE; Chemistry; Chemistry, Multidisciplinary; DNA structures; duplex stability; GLYCOSIDIC CONFORMATION; HAIRPIN FORMATION; nucleosides; OLIGODEOXYNUCLEOTIDES; oligonucleosides; PROPYNE ANALOGS; SUGAR CONFORMATION
Erscheinungsdatum: 1998
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMISTRY-A EUROPEAN JOURNAL
Volumen: 4
Ausgabe: 9
Startseite: 1781
Seitenende: 1790
Zusammenfassung: 
Oligonucleotides containing 7-deaza-7-(hex-1-ynyl)-2'-deoxyadenosine (1) and 7-deaza-7-iodo-2'-deoxyadenosine (2) are described. The corresponding phosphoramidites (3 a,b) were synthesized and employed in solid-phase oligonucleotide synthesis. The modified 7-deazaadenine residues show selective base-pairing with dT. According to the T-m values and the thermodynamic data of duplex formation, the 7-iodo and the 7-(hex-1-ynyl) residues of a 7-deazaadenine moiety increase the duplex stability with retention of the particular DNA structure. This is different from 8-substituted adenine, which destabilizes the nucleic acid duplex significantly. The nucleoside 1 fluoresces strongly.
ISSN: 09476539
DOI: 10.1002/(SICI)1521-3765(19980904)4:9<1781::AID-CHEM1781>3.0.CO;2-K

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