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Modular quadruplex-duplex hybrids as biomolecular scaffolds for asymmetric Michael addition reactions.
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2020-09-01 , DOI: 10.1039/d0ob01362e
Ji Hye Yum 1 , Hiroshi Sugiyama , Soyoung Park
Affiliation  

Asymmetric synthesis based on DNA scaffolds has been actively exploited because of the advantages of DNA such as diverse tertiary structures, chemical stability, and easy handling. Since duplex DNA-based hybrid catalysts have demonstrated this remarkable capability, efforts have been made to investigate new biomolecular scaffolds. Herein, we report modular quadruplex–duplex (QD) hybrid DNA catalysts containing bipyridine ligands and hydrogen donor moieties. The conformation, thermal stability, and metal-binding ability of modified QD hybrid DNA were characterized using spectroscopy. The QD hybrid-based DNA catalysts were successfully applied to asymmetric Michael addition reactions (86% conversion and 76% ee). This study describes a new type of DNA hybrid catalyst produced by the construction of a cooperative active site with a Lewis acid and a H-bond donor.

中文翻译:

模块化四链体-双链体杂化物作为不对称迈克尔加成反应的生物分子支架。

由于 DNA 具有多种三级结构、化学稳定性和易于处理等优点,基于 DNA 支架的不对称合成已被积极利用。由于基于双链 DNA 的杂化催化剂已经证明了这种卓越的能力,因此人们努力研究新的生物分子支架。在此,我们报告了含有联吡啶配体和氢供体部分的模块化四链体-双链体 (QD) 杂化 DNA 催化剂。使用光谱学表征了修饰的 QD 杂合 DNA 的构象、热稳定性和金属结合能力。基于 QD 杂化的 DNA 催化剂成功地应用于不对称迈克尔加成反应(86% 转化率和 76% ee)。
更新日期:2020-09-16
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