Related Experiment Video
Updated: Jun 25, 2025

08:51
Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
Published on: August 18, 2017
10.3K
Update on chiral recognition mechanisms in separation science
1Department of Pharmaceutical/Medicinal Chemistry, Friedrich Schiller University, Jena, Germany.
Journal of Separation Science
|May 21, 2024
Summary
Understanding chiral recognition mechanisms is crucial for stereospecific analysis. This review highlights recent advances in chiral selectors, combining separation techniques with molecular modeling and spectroscopy.
Area of Science:
- Analytical Chemistry
- Separation Science
- Stereochemistry
Background:
- Stereospecific analysis of chiral molecules is vital across scientific disciplines.
- Chiral separation relies on forming transient diastereomeric complexes between selectors and selectand enantiomers.
- Molecular interactions like electrostatic, dipole-dipole, and hydrogen bonds drive selector-selectand complexation.
Purpose of the Study:
- To review recent advancements (2020-2024) in understanding chiral recognition mechanisms.
- To highlight the synergy between separation techniques and molecular modeling/spectroscopy.
- To provide an overview of various important chiral selectors.
Main Methods:
- Review of literature combining separation techniques with molecular modeling and/or spectroscopic methods.
- Analysis of studies focusing on chiral selector-selectand interactions.
- Focus on advancements between 2020 and early 2024.
Main Results:
- Summarizes recent achievements in understanding chiral recognition for key selectors.
- Covers polysaccharide derivatives, cyclodextrins, macrocyclic glycopeptides, proteins, and more.
- Includes insights into chiral ionic liquids and deep eutectic solvents.
Conclusions:
- Recent research has significantly advanced the understanding of chiral recognition mechanisms.
- The integration of separation science with computational and spectroscopic methods is key.
- This review provides a valuable snapshot of current progress in chiral separation science.
Related Concept Videos
Chirality in Nature
13.3K
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.
13.3K
Prochirality
3.8K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
3.8K
Racemic Mixtures and the Resolution of Enantiomers
18.3K
A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit...
18.3K
Chirality
24.0K
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...
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...
24.0K
Chirality at Nitrogen, Phosphorus, and Sulfur
5.7K
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...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
5.7K
Molecules with Multiple Chiral Centers
11.6K
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...
11.6K

