Stereochemical study on planar-chiral cyclic molecules using polysaccharide-based column chromatography

Kazunobu Igawa; Kazuhiro Uehara; Yuuya Kawasaki; Katsuhiko Tomooka

doi:10.1002/chir.23429

Stereochemical study on planar-chiral cyclic molecules using polysaccharide-based column chromatography

Kazunobu Igawa, Kazuhiro Uehara, Yuuya Kawasaki, Katsuhiko Tomooka

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Review article › peer-review

1 Citation (Scopus)

Abstract

The presence of planar chirality of a variety of medium-sized heterocycles, along with nine-membered cyclic ketone and its enol ester, was revealed by observation of isolable enantiomers by analytical high-performance liquid chromatography (HPLC) using a chiral stationary phase with a polysaccharide-based chiral selector. Several tens of milligrams of enantiomers of the planar-chiral molecules were successfully separated by preparative-scale HPLC, leading to the preparation of an enantioenriched sample. This in turn enabled detailed stereochemical studies, including measurement of half-lives of the optical activity and X-ray crystallography for elucidation of stereochemistry.

Original language	English
Journal	Chirality
DOIs	https://doi.org/10.1002/chir.23429
Publication status	Accepted/In press - 2022

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/chir.23429

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title = "Stereochemical study on planar-chiral cyclic molecules using polysaccharide-based column chromatography",

abstract = "The presence of planar chirality of a variety of medium-sized heterocycles, along with nine-membered cyclic ketone and its enol ester, was revealed by observation of isolable enantiomers by analytical high-performance liquid chromatography (HPLC) using a chiral stationary phase with a polysaccharide-based chiral selector. Several tens of milligrams of enantiomers of the planar-chiral molecules were successfully separated by preparative-scale HPLC, leading to the preparation of an enantioenriched sample. This in turn enabled detailed stereochemical studies, including measurement of half-lives of the optical activity and X-ray crystallography for elucidation of stereochemistry.",

author = "Kazunobu Igawa and Kazuhiro Uehara and Yuuya Kawasaki and Katsuhiko Tomooka",

note = "Funding Information: This research was supported by JSPS KAKENHI Grants (JP20H05677, JP20H02743) and the Cooperative Research Program of “Network Joint Research Center for Materials and Devices.” This work was carried out by using the research equipment shared in the MEXT Project for promoting the public utilization of advanced research infrastructure (Program for supporting the introduction of the new sharing system), Grant Number JPMXS0422300120. Publisher Copyright: {\textcopyright} 2022 Wiley Periodicals LLC.",

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doi = "10.1002/chir.23429",

language = "English",

journal = "Chirality",

issn = "0899-0042",

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TY - JOUR

T1 - Stereochemical study on planar-chiral cyclic molecules using polysaccharide-based column chromatography

AU - Igawa, Kazunobu

AU - Uehara, Kazuhiro

AU - Kawasaki, Yuuya

AU - Tomooka, Katsuhiko

N1 - Funding Information: This research was supported by JSPS KAKENHI Grants (JP20H05677, JP20H02743) and the Cooperative Research Program of “Network Joint Research Center for Materials and Devices.” This work was carried out by using the research equipment shared in the MEXT Project for promoting the public utilization of advanced research infrastructure (Program for supporting the introduction of the new sharing system), Grant Number JPMXS0422300120. Publisher Copyright: © 2022 Wiley Periodicals LLC.

PY - 2022

Y1 - 2022

N2 - The presence of planar chirality of a variety of medium-sized heterocycles, along with nine-membered cyclic ketone and its enol ester, was revealed by observation of isolable enantiomers by analytical high-performance liquid chromatography (HPLC) using a chiral stationary phase with a polysaccharide-based chiral selector. Several tens of milligrams of enantiomers of the planar-chiral molecules were successfully separated by preparative-scale HPLC, leading to the preparation of an enantioenriched sample. This in turn enabled detailed stereochemical studies, including measurement of half-lives of the optical activity and X-ray crystallography for elucidation of stereochemistry.

AB - The presence of planar chirality of a variety of medium-sized heterocycles, along with nine-membered cyclic ketone and its enol ester, was revealed by observation of isolable enantiomers by analytical high-performance liquid chromatography (HPLC) using a chiral stationary phase with a polysaccharide-based chiral selector. Several tens of milligrams of enantiomers of the planar-chiral molecules were successfully separated by preparative-scale HPLC, leading to the preparation of an enantioenriched sample. This in turn enabled detailed stereochemical studies, including measurement of half-lives of the optical activity and X-ray crystallography for elucidation of stereochemistry.

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U2 - 10.1002/chir.23429

DO - 10.1002/chir.23429

M3 - Review article

C2 - 35403298

AN - SCOPUS:85127775446

SN - 0899-0042

JO - Chirality

JF - Chirality

ER -

Stereochemical study on planar-chiral cyclic molecules using polysaccharide-based column chromatography

Abstract

All Science Journal Classification (ASJC) codes

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