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      Characteristic and complementary chiral recognition ability of four recently developed immobilized chiral stationary phases based on amylose and cellulose phenyl carbamates and benzoates

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          Abstract

          To date, various immobilized chiral stationary phases (CSPs) have been developed. The immobilized CSPs have opened up possibilities not only maintaining the high chiral recognition abilities as well as corresponding coated ones but also affording high durability to various mobile phase. This report directed to investigate enantioseparation of recently launched four immobilized CSPs with cellulose and amylose backbones under normal phase liquid chromatography conditions. Their chiral recognition abilities were compared with previously developed six immobilized CSPs. Particularly, we focused on the complementarity for chiral recognitions. Among them, amylose tris(3‐chloro‐5‐methylphenylcarbamate) CSP, namely, CHIRALPAK IG, showed notable chiral recognition abilities to various racemates. As expected, the investigated immobilized CSPs represented remarkable durability to wide range of mobile phases, whereas the corresponding coated CSPs could not be run due to the irreversible degradation. Taking advantage of unrestricted solvent compatibility, chiral separation selectivities were improved for some racemates.

          Abstract

          The chiral recognition ability and durability toward to polar organic solvents regarding four recently developed immobilized chiral stationary phases based on amylose tris(3‐chloro‐5‐methylphenylcarbamate), cellulose tris(3‐chloro‐5‐methylphenylcarbamate), amylose tris[( S)‐phenylethylcarbamate], and cellulose tris(4‐methylbenzoate) was investigated and summarized.

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          Most cited references41

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          Efficient Separation of Enantiomers Using Stereoregular Chiral Polymers.

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            Polysaccharide Derivatives for Chromatographic Separation of Enantiomers

            The first resolution of enantiomers was performed 150 years ago-mechanically. Today a powerful method for carrying out this task is HPLC on polysaccharide derivatives as chiral stationary phases. Most racemates, from an analytical to a preparative scale, now appear to be resolved by this technique. As an example, the chromatogram for the enantiomeric resolution of a fullerene derivative is shown on the right.
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              Chiral HPLC for efficient resolution of enantiomers.

              Resolution of racemic compounds is one of the potential ways of obtaining both enantiomers. Among several resolution techniques in the past few decades, direct enantioseparation by high-performance liquid chromatography (HPLC) has significantly advanced, and a large number of chiral stationary phases (CSPs) for HPLC have been developed using both chiral small molecules and polymers with chiral recognition abilities. In this tutorial review, after describing the brief history and general view of CSPs, special emphasis will be placed on the studies involving the development and application of polysaccharide-based CSPs in our group.
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                Author and article information

                Contributors
                tk_onishi@jp.daicel.com
                Journal
                Chirality
                Chirality
                10.1002/(ISSN)1520-636X
                CHIR
                Chirality
                John Wiley and Sons Inc. (Hoboken )
                0899-0042
                1520-636X
                12 April 2022
                July 2022
                : 34
                : 7 ( doiID: 10.1002/chir.v34.7 )
                : 925-940
                Affiliations
                [ 1 ] DAICEL Corporation, CPI Company, Analytical Tools BU Research and Development Center Arai Factory Myoko Niigata Japan
                Author notes
                [*] [* ] Correspondence

                Takafumi Onishi, DAICEL Corporation, CPI Company, Analytical Tools BU Research and Development Center, Arai Factory, 1‐1, Shinko‐cho, Myoko, Niigata 944‐8550, Japan.

                Email: tk_onishi@ 123456jp.daicel.com

                Author information
                https://orcid.org/0000-0003-3547-6925
                Article
                CHIR23446
                10.1002/chir.23446
                9321961
                35413148
                ea04f205-560f-45cf-b759-179fe3fc3c30
                © 2022 Daicel Corporation. Chirality published by Wiley Periodicals LLC.

                This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

                History
                : 15 March 2022
                : 29 November 2021
                : 18 March 2022
                Page count
                Figures: 13, Tables: 2, Pages: 16, Words: 8112
                Categories
                Research Article
                Special Issue: A Special Issue to Celebrate the 80th Birthday of Professor Yoshio Okamoto
                Research Article
                Custom metadata
                2.0
                July 2022
                Converter:WILEY_ML3GV2_TO_JATSPMC version:6.1.7 mode:remove_FC converted:26.07.2022

                General chemistry
                comparison between coated type and immobilized type,complementary properties and solvent resistance,enantiomer resolution by hplc,immobilized polysaccharide‐based chiral stationary phases

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