2-Aminopyridine as a Nucleobase Substitute for Adenine in DNA-like Architectures: Synthesis of Alkynyl C-Nucleotides and Their Hybridization Characteristics
2-Aminopyridine as a Nucleobase Substitute for Adenine in DNA-like Architectures: Synthesis of Alkynyl C-Nucleotides and Their Hybridization Characteristics
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2-氨基吡啶作为 DNA 样结构中腺嘌呤的核碱基替代物：炔基 C-核苷酸的合成及其杂交特征
DOI：
10.1021/acs.joc.9b02750
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发表时间：
2019
期刊：
影响因子：
--
通讯作者：
Inouye Masahiko
中科院分区：
文献类型：
--
作者：
Kurosaki Fumihiro;Chiba Junya;Oda Yutaro;Hino Airi;Inouye Masahiko
将卤代2-氨基吡啶作为核碱基替代物连接到乙炔基C-2-脱氧-β-d-呋喃核苷的乙炔末端，然后将C-核苷掺入天然DNA中。所得嵌合DNA与互补嵌合DNA构建了双螺旋结构。在双链体中，2-氨基吡啶充当腺嘌呤类似物，与非天然胸腺嘧啶等排体形成碱基对。还仅从腺嘌呤型C-核苷制备了人工同聚寡聚物，并证明与相应的人工胸腺嘧啶型同聚寡聚物形成完全人工双螺旋。
Halogenated 2-aminopyridine was attached to the acetylene terminal of ethynylC-2-deoxy-β-d-ribofuranoside as a nucleobase substitute, and then, theC-nucleoside was incorporated into natural DNAs. The resulting chimeric DNA constructed double helical structures with the complementary chimeric DNA. In the duplex, 2-aminopyridine functioned as an adenine analogue that formed a base pair with a non-natural thymine isostere. Artificial homooligomers were also prepared only from the adenine-typeC-nucleoside and proven to form completely artificial double helices with the corresponding artificial thymine-type homooligomers.