Adv Polym Sci (2013) 261: 391–414
DOI: 10.1007/12_2013_240
© Springer-Verlag Berlin Heidelberg 2013
Published online: 20 October 2013
Helical Polymers for Efficient Enantiomer
Separation
Yoshio Okamoto
Abstract The separation of enantiomers by high-performance liquid chromatography (HPLC) using the helical polymers mainly synthesized in my group over the
past 40 years is described. In 1979, a one-handed helical poly(triphenylmethyl
methacrylate) (PTrMA) was synthesized by asymmetric anionic polymerization.
This is the first example of the asymmetric synthesis of a one-handed helical
polymer, and the polymer exhibited an unexpected high chiral recognition to
many racemates. A practically useful chiral stationary phase (CSP) for HPLC
was developed by coating the polymer on silica gel. In 1982, the CSP was
commercialized as the first chiral column based on a chiral polymer. Following
this study, various helical polymers have been synthesized for use as CSPs by many
researchers including ourselves and, in many cases, the helical structure of the
polymers has played an important role in chiral recognition. In 1984, we found that
cellulose trisphenylcarbamate coated on silica gel showed a very high chiral
recognition and afforded a very useful CSP. Among the many phenylcarbamate
derivatives of cellulose and amylose, the tris(3,5-dimethylphenylcarbamate)s show
very attractive abilities. Today, these polysaccharide-based CSPs are most
frequently used to analyze or preparatively separate chiral compounds.
Keywords 3,5-Dimethylphenylcarbamate Á Chiral recognition Á Chiral stationary
phase Á Enantioseparation Á Helix
Y. Okamoto (*)
Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
Polymer Materials Research Center, Harbin Engineering University, Harbin, China
e-mail: okamoto@apchem.nagoya-u.ac.jp
DOI: 10.1007/12_2013_240
© Springer-Verlag Berlin Heidelberg 2013
Published online: 20 October 2013
Helical Polymers for Efficient Enantiomer
Separation
Yoshio Okamoto
Abstract The separation of enantiomers by high-performance liquid chromatography (HPLC) using the helical polymers mainly synthesized in my group over the
past 40 years is described. In 1979, a one-handed helical poly(triphenylmethyl
methacrylate) (PTrMA) was synthesized by asymmetric anionic polymerization.
This is the first example of the asymmetric synthesis of a one-handed helical
polymer, and the polymer exhibited an unexpected high chiral recognition to
many racemates. A practically useful chiral stationary phase (CSP) for HPLC
was developed by coating the polymer on silica gel. In 1982, the CSP was
commercialized as the first chiral column based on a chiral polymer. Following
this study, various helical polymers have been synthesized for use as CSPs by many
researchers including ourselves and, in many cases, the helical structure of the
polymers has played an important role in chiral recognition. In 1984, we found that
cellulose trisphenylcarbamate coated on silica gel showed a very high chiral
recognition and afforded a very useful CSP. Among the many phenylcarbamate
derivatives of cellulose and amylose, the tris(3,5-dimethylphenylcarbamate)s show
very attractive abilities. Today, these polysaccharide-based CSPs are most
frequently used to analyze or preparatively separate chiral compounds.
Keywords 3,5-Dimethylphenylcarbamate Á Chiral recognition Á Chiral stationary
phase Á Enantioseparation Á Helix
Y. Okamoto (*)
Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
Polymer Materials Research Center, Harbin Engineering University, Harbin, China
e-mail: okamoto@apchem.nagoya-u.ac.jp