2021 Fiscal Year Final Research Report

Absolute asymmetric synthesis via helix-sense-selective polymerization and selective degradation reaction using circularly polarized light as asymmetric source

Research Project

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Project/Area Number	19K05453
Research Category	Grant-in-Aid for Scientific Research (C)
Allocation Type	Multi-year Fund
Section	一般
Review Section	Basic Section 33020:Synthetic organic chemistry-related
Research Institution	Niigata University
Principal Investigator	TERAGUCHI Masahiro 新潟大学, 自然科学系, 助教 (30334650)
Co-Investigator(Kenkyū-buntansha)	青木俊樹新潟大学, 自然科学系, 教授 (80212372) 金子隆司新潟大学, 自然科学系, 教授 (90272856)
Project Period (FY)	2019-04-01 – 2022-03-31
Keywords	円偏光 / らせん選択重合 / らせん巻き方向選択分解 / 環化芳香族化分解 / 光学分割
Outline of Final Research Achievements	In this research project, we investigated a method for producing optically active compounds without using any optically active compounds as a chiral source by utilizing helix-sense-selective polymerization and helix-sense-selective degradation by circular polarized light. It was shown that the chiral aggregation derived from an achiral monomer may caused the spontaneous helix-sense-selective polymerization in the absence of a chiral source. In addition, optical resolution of racemic mixture of alcohol was successfully achieved by enantioselective helix-sense-selcetive polymerization of a monomer synthesized from a racemic mixture of chiral alcohol, followed by helix-sense-selective degradation of the obtained polymer by irradiation of circularly polarized light. The optical yields of the obtained alcohol were high. Therefore, optical resolution was achieved with high optical yield without the use of any optically active compounds.
Free Research Field	機能性高分子合成
Academic Significance and Societal Importance of the Research Achievements	人体を構成する主物質であるタンパク質はアミノ酸からなる。アミノ酸など自然界に存在する分子の多くは右手、左手の関係に相当する鏡像異性体（エナンチオマー）が存在しうるにも関わらず、自然界にはいずれか一方が独占的に存在している。近年、小惑星探査により地球外の天体にアミノ酸の一方のエナンチオマーの存在が確認され、どのようにして一方のエナンチオマーへと偏りが生じたのかについてますます関心が持たれている。本研究は自然界のキラリティーの偏りに至る過程に光（円偏光）が関与するモデルとして学術的意義があるだけでなく、光を不斉源とする光学分割法も新たに提案し、社会的・実用的な意義を有する。