Journal
PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES
Volume 91, Issue 6, Pages 246-261Publisher
JAPAN ACAD
DOI: 10.2183/pjab.91.246
Keywords
asymmetric polymerization; helix-sense-selective polymerization; sparteine; chiral recognition; chiral stationary phase; enantioseparation
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Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan
- Daicel Corporation
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Helical structures are chiral, which means that if we can synthesize a polymer having a stable one-handed helicity, the polymer is optically active. In 1979, we succeeded in the synthesis of a one-handed helical polymer from an optically inactive achiral monomer, triphenylmethyl methacrylate (TrMA). This is the first example of the asymmetric synthesis of an optically active one-handed helical polymer. The polymer (PTrMA) exhibited an unexpected high chiral recognition ability and afforded a practically useful chiral stationary phase (CSP) for high-performance liquid chromatography (HPLC) by coating it on silica gel. In addition, we also succeeded in the development of very useful CSPs for HPLC using the phenylcarbamate derivatives of polysaccharides, cellulose and amylose. These CSPs can efficiently resolve a broad range of chiral compounds, and have been used all over the world for separating and analyzing chiral compounds.
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