Photoinduced Changes in Hydrogen Bonding Patterns of 8-Thiopurine Nucleobase Analogues in a DNA Strand.
Photoinduced Changes in Hydrogen Bonding Patterns of 8-Thiopurine Nucleobase Analogues in a DNA Strand.
复制标题
DNA 链中 8-硫代嘌呤核碱基类似物的氢键模式的光诱导变化。
DOI：
10.1039/c3ob42427h
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发表时间：
2014
期刊：
影响因子：
--
通讯作者：
S. Obika
中科院分区：
文献类型：
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作者：
K. Morihiro;T. Kodama;S. Mori;S. Obika
碱基之间形成的氢键（H-键）在各种核酸结构的构建中起重要作用。核碱基的H-供体和H-受体模式负责选择性和正确的碱基对形成。在此，我们描述了8-硫代腺嘌呤核碱基类似物和8-硫代次黄嘌呤核碱基类似物，其在硫原子上具有光不稳定的6-硝基藜芦基（NV）基团（分别为SANV和SHNV）。光触发的NV基团的去除导致SANV和SHNV的互变异构化和氢键模式的变化。氢键模式的这种变化对8-巯基嘌呤核碱基类似物的碱基识别有很强的影响。特别是，SHNV的碱基识别在光照射后明显从鸟嘌呤转移到腺嘌呤。这些结果表明，光诱导的氢键模式的变化是一种独特的策略，用于操纵核酸组装与时空控制。
Hydrogen bonds (H-bonds) formed between nucleobases play an important role in the construction of various nucleic acid structures. The H-donor and H-acceptor pattern of a nucleobase is responsible for selective and correct base pair formation. Herein, we describe an 8-thioadenine nucleobase analogue and an 8-thiohypoxanthine nucleobase analogue with a photolabile 6-nitroveratryl (NV) group on the sulfur atom (SANV and SHNV, respectively). Light-triggered removal of the NV group causes tautomerization and a change in the H-bonding pattern of SANV and SHNV. This change in the H-bonding pattern has a strong effect on base recognition by 8-thiopurine nucleobase analogues. In particular, base recognition by SHNV is clearly shifted from guanine to adenine upon photoirradiation. These results show that a photoinduced change in the H-bonding pattern is a unique strategy for manipulating nucleic acid assembly with spatiotemporal control.