Synthesis of 8-aza-3,7-dideaza-2'-deoxyadenosines possessing a new adenosine skeleton as an environmentally sensitive fluorescent nucleoside for monitoring DNA minor groove
Synthesis of 8-aza-3,7-dideaza-2'-deoxyadenosines possessing a new adenosine skeleton as an environmentally sensitive fluorescent nucleoside for monitoring DNA minor groove
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具有新腺苷骨架的8-氮杂-3,7-二脱氮杂-2-脱氧腺苷的合成作为环境敏感荧光核苷用于监测DNA小沟
DOI：
10.1039/c5ob00862j
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发表时间：
2015
影响因子：
3.2
通讯作者：
Yoshio Saito
中科院分区：
文献类型：
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作者：
Azusa Suzuki;Mio Saito;Ryuzi Katoh;Yoshio Saito
首次合成了8-叠氮-3,7-二氮杂-2 ' -脱氧腺苷1及其c3 -萘乙基化衍生物3n7zA(2)，其中含有8-叠氮-3,7-二氮杂嘌呤（吡唑[4,3-c]吡啶）骨架。特别是，核苷3n7zA(2)表现出环境敏感的分子内电荷转移（ICT）发射，这是由于核碱基和萘基组成的共面构象中的电子跃迁。将其结合到寡脱氧核苷酸（ODN）探针中，通过发射波长的明显变化，可以清楚地识别互补链中完美匹配的胸腺嘧啶(T)。此外，3n7zA(2)两侧含有胞嘧啶/鸟嘌呤（C/G）碱基对的双链只有在修饰核苷的对端碱基不匹配时才会被鸟嘌呤强烈猝灭，从而增强了其碱基识别能力。因此，含有3n7zA(2)的ODN探针可作为同质单核苷酸多态性（SNP）分型的有效报告探针。
8-Aza-3,7-dideaza-2′-deoxyadenosine 1 and its C3-naphthylethynylated derivative 3n7zA (2) comprising a 8-aza-3,7-dideazapurine (pyrazolo[4,3-c]pyridine) skeleton were synthesized for the first time. In particular, nucleoside 3n7zA (2) exhibited environmentally sensitive intramolecular charge transfer (ICT) emission because of electron transition in the coplanar conformer formed by nucleobase and naphthalene moieties. Its incorporation into oligodeoxynucleotide (ODN) probes enable a clear identification of a perfectly matched thymine (T) in the complementary strand by a distinct change in the emission wavelength. In addition, the fluorescence emission of the duplexes containing a cytosine/guanine (C/G) base pair flanking 3n7zA (2) was strongly quenched by guanine only when the opposite base of the modified nucleoside was mismatched, enhancing its base identification ability. Thus, ODN probes containing 3n7zA (2) acted as effective reporter probes for homogeneous single nucleotide polymorphism (SNP) typing.