Ken Yamada, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine
{"title":"Synthesis and hybridization properties of oligonucleotides having 4-N-(pyrrol-2-ylcarbonyl)deoxycytidine.","authors":"Ken Yamada, Hirosuke Tsunoda, Akihiro Ohkubo, Kohji Seio, Mitsuo Sekine","doi":"10.1093/nass/nrp058","DOIUrl":null,"url":null,"abstract":"<p><p>A new 4-N-acylated deoxycytidine derivative, 4-N-(1H-pyrrol-2-ylcarbonyl)deoxycytidine, was synthesized and found to be stable under rather basic conditions. Oligodeoxynucleotides (ODNs) incorporating this modified deoxynucleoside at various positions were successfully synthesized by using a pivaloyloxymethyl (POM) group for protection of the pyrrole residue. The POM group was removed by treatment with 1.5 M NaOMe/MeOH. ODNs containing modified deoxycytidines exhibited hybridization properties superior to those of the unmodified ODNs. We found the acylation of the cytosine base with an aromatic acyl-type substituent led to significant increase of the thermo stability of DNA duplexes. This is the first noteworthy observation in this kind of modification. The synthesis and hybridization properties of 4-N-(1H-pyrrol-2-ylcarbonyl)deoxycytidine derivatives will be also reported.</p>","PeriodicalId":87448,"journal":{"name":"Nucleic acids symposium series (2004)","volume":" 53","pages":"115-6"},"PeriodicalIF":0.0000,"publicationDate":"2009-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1093/nass/nrp058","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Nucleic acids symposium series (2004)","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1093/nass/nrp058","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A new 4-N-acylated deoxycytidine derivative, 4-N-(1H-pyrrol-2-ylcarbonyl)deoxycytidine, was synthesized and found to be stable under rather basic conditions. Oligodeoxynucleotides (ODNs) incorporating this modified deoxynucleoside at various positions were successfully synthesized by using a pivaloyloxymethyl (POM) group for protection of the pyrrole residue. The POM group was removed by treatment with 1.5 M NaOMe/MeOH. ODNs containing modified deoxycytidines exhibited hybridization properties superior to those of the unmodified ODNs. We found the acylation of the cytosine base with an aromatic acyl-type substituent led to significant increase of the thermo stability of DNA duplexes. This is the first noteworthy observation in this kind of modification. The synthesis and hybridization properties of 4-N-(1H-pyrrol-2-ylcarbonyl)deoxycytidine derivatives will be also reported.
合成了一种新的4-N-酰基化脱氧胞苷衍生物，4-N-(1h -吡咯-2-羰基)脱氧胞苷，并在较碱性条件下具有稳定性。利用聚戊酰氧甲基(POM)保护吡咯残基，在不同位置成功合成了含有该修饰脱氧核苷的寡脱氧核苷酸(odn)。用1.5 M NaOMe/MeOH处理POM组。含有修饰脱氧胞苷的odn表现出优于未修饰odn的杂交特性。我们发现胞嘧啶碱基与芳香酰基型取代基的酰化导致DNA双链的热稳定性显著提高。这是这种修正中第一个值得注意的观察结果。本文还报道了4-N-(1h -吡咯-2-羰基)脱氧胞苷衍生物的合成及其杂化性质。
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
