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Chirality

Chirality

Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...

Chirality in Nature

Chirality in Nature

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.

Molecules with Multiple Chiral Centers

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

Affinity Chromatography

Affinity Chromatography

Affinity chromatography is a powerful technique extensively utilized for separating and purifying specific biomolecules from complex mixtures. It capitalizes on the highly selective binding between an analyte and its counterpart, such as antibody-antigen interactions. The counterpart is immobilized on the stationary phase, forming an affinity column. The stationary phase typically consists of solid support, such as agarose or porous glass beads, immobilizing the affinity ligand. The mobile...

Chromatography: Introduction

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Chromatography is a technique used to separate compounds based on differences of partitioning between two phases, the stationary phase and the mobile phase.
The phase in which the compounds linger or on which the compounds adsorb is called the stationary phase, whereas the mobile phase is the solvent that carries the solutes to be analyzed. In traditional column chromatography, the mixture flows through the stationary phase, and the compounds partition between the stationary and mobile phases...

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Related Experiment Video

Updated: Jan 25, 2026

A Micropatterning Assay for Measuring Cell Chirality

A Micropatterning Assay for Measuring Cell Chirality

Published on: March 11, 2022

Chiral Separations by Countercurrent Chromatography.

Sheng-Qiang Tong¹

¹College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, People's Republic of China. sqtong@zjut.edu.cn.

Methods in Molecular Biology (Clifton, N.J.)

|May 10, 2019

Summary

This summary is machine-generated.

This study presents two high-speed countercurrent chromatography methods for separating enantiomers of phenylsuccinic acid and alpha-hydroxy acids. Hydroxypropyl-beta-cyclodextrin and N-n-dodecyl-L-proline were used as chiral selectors for effective chiral separations.

Keywords:

Biphasic solvent system Chiral ligand exchange Chiral separation Countercurrent chromatography Homogeneous chiral selector

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Area of Science:

Analytical Chemistry
Separation Science
Organic Chemistry

Background:

Countercurrent chromatography (CCC) is a liquid-liquid separation technique.
Chiral separations are crucial for distinguishing enantiomers in pharmaceuticals and agrochemicals.
Two primary modes exist for chiral CCC: homogeneous chiral selector addition and interfacial chiral ligand exchange.

Purpose of the Study:

To describe two novel high-speed countercurrent chromatography (HSCCC) methods for enantioseparation.
To demonstrate the application of specific chiral selectors in HSCCC.
To achieve the separation of phenylsuccinic acid and alpha-hydroxy acids enantiomers.

Main Methods:

High-speed countercurrent chromatography (HSCCC) was employed.
Two chiral separation modes were utilized: homogeneous chiral selector addition and interfacial chiral ligand exchange.
Hydroxypropyl-β-cyclodextrin (HP-β-CD) and N-n-dodecyl-L-proline were used as chiral selectors.

Main Results:

Successful enantioseparation of phenylsuccinic acid was achieved using both methods.
Effective separation of α-hydroxy acids enantiomers was demonstrated.
The study validated the utility of HP-β-CD and N-n-dodecyl-L-proline in HSCCC for chiral resolutions.

Conclusions:

HSCCC is a viable technique for chiral separations.
The selected chiral selectors and methods are effective for resolving phenylsuccinic acid and α-hydroxy acids.
This work contributes to the advancement of enantioseparation techniques in chromatography.