Synthesis and characterization of oligodeoxynucleotides containing a novel tetraazabenzo[cd]azulene:naphthyridine base pair
Synthesis and characterization of oligodeoxynucleotides containing a novel tetraazabenzo[cd]azulene:naphthyridine base pair
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含有新型四氮杂苯并[cd]甘菊环:萘啶碱基对的寡脱氧核苷酸的合成和表征
DOI：
10.1016/j.bmc.2010.11.023
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发表时间：
2011
期刊：
影响因子：
--
通讯作者：
and Akira Matsuda
中科院分区：
文献类型：
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作者：
Yasuyuki Hirama;Noriaki Minakawa;and Akira Matsuda
介绍了含4-氨基-2,3,5,6-四氮杂氮并[cd]azulen-7- 1核苷5 （BaON）的寡脱氧核苷酸（ODNs）的合成及其热稳定性，目的是开发新的碱基配对基序。以7-二氮杂-7-碘嘌呤衍生物1为原料，经钯催化与丙烯酸甲酯交叉偶联反应制备三环核苷5，并进行分子内环化反应。将得到的核苷加入到odn中，并通过热变性研究评价了双相中BaON:NaNO（2-氨基-7-羟基-1,8-萘啶核苷）对的碱基配对性质。含有BaON:NaNOpair的双链的熔融温度Tm值高于含有腺嘌呤-胸腺嘧啶（a:T）和鸟嘌呤-胞嘧啶（G:C）对的双链，但低于含有ImON:NaNO（ImON=7-氨基咪唑[5 ',4 ':4,5]吡啶[2,3-d]嘧啶-4(5H)- 1核苷）对的双链。一项温度相关的1h NMR研究表明，BaON的氢键能力低于ImON，这可以解释为什么BaON:NaNOpair的热稳定性不如ImON:NaNOpair。
The synthesis and thermal stability of oligodeoxynucleotides (ODNs) containing 4-amino-2,3,5,6-tetraazabenzo[cd]azulen-7-one nucleosides 5 (BaON) with the aim of developing new base pairing motif is described. The tricyclic nucleoside 5 was prepared starting with the 7-deaza-7-iodopurine derivative 1 via a palladium catalyzed cross-coupling reaction with methyl acrylate, followed by an intramolecular cyclization. The resulting nucleoside was incorporated into ODNs, and the base pairing property of the BaON:NaNO(2-amino-7-hydroxy-1,8-naphthyridine nucleoside) pair in the duplex was evaluated by a thermal denaturation study. The melting temperature (Tm) of the duplex containing the BaON:NaNOpair showed a higher value than that of the duplexes containing the adenine:thymine (A:T) and the guanine:cytosine (G:C) pairs, however it was lower than that of the ImON:NaNO(ImON=7-amino-imidazo[5′,4′:4,5]pyrido[2,3-d]pyrimidin-4(5H)-one nucleoside) pair. A temperature-dependent1H NMR study revealed that the H-bonding ability of BaONwas lower than that of ImON, which would explain why the BaON:NaNOpair was less thermally stable than the ImON:NaNOpair.