8-氮杂-7-脱氮-2'-脱氧异鸟苷及其7-卤代衍生物在具有平行和反平行链取向的寡核苷酸双链体中的碱基配对特性。
The base pairing properties of 8-aza-7-deaza-2'-deoxyisoguanosine and 7-halogenated derivatives in oligonucleotide duplexes with parallel and antiparallel chain orientation.
作者信息
Seela Frank, Kröschel Rita
机构信息
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany.
出版信息
Nucleic Acids Res. 2003 Dec 15;31(24):7150-8. doi: 10.1093/nar/gkg926.
Abstract
The base pairing properties of oligonucleotide duplexes containing 8-aza-7-deaza-2'-deoxyisoguanosine, its 7-bromo or its 7-iodo derivative are described. The nucleosides were synthesized on a convergent route, protected and converted into phosphoramidites. Oligonucleotides were prepared on a solid-phase and were hybridized to yield duplexes with parallel (ps) or antiparallel (aps) chain orientation. The 8-aza-7-deaza-2'-deoxyisoguanosine-containing duplexes show almost identical base pairing stability as those containing 2'-deoxyisoguanosine, while the 7-substituted derivatives induce a significant duplex stabilization both in ps and aps DNA. Self-complementary duplexes with parallel chain orientation are exceptionally stable due to the presence of 5'-overhangs. The bulky halogen substituents were found to be well accommodated in the grooves both of aps and ps DNA.
摘要
描述了含有8-氮杂-7-脱氮-2'-脱氧异鸟苷、其7-溴或7-碘衍生物的寡核苷酸双链体的碱基配对特性。核苷通过汇聚路线合成，进行保护并转化为亚磷酰胺。寡核苷酸在固相上制备，并进行杂交以产生具有平行（ps）或反平行（aps）链取向的双链体。含8-氮杂-7-脱氮-2'-脱氧异鸟苷的双链体显示出与含2'-脱氧异鸟苷的双链体几乎相同的碱基配对稳定性，而7-取代衍生物在ps和aps DNA中均诱导显著的双链体稳定化。由于存在5'-突出端，具有平行链取向的自互补双链体异常稳定。发现庞大的卤素取代基能很好地容纳在aps和ps DNA的沟槽中。
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