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Prochirality

Prochirality

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...

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.

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...

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...

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...

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Related Experiment Video

Updated: Jul 14, 2025

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

Chirality: a key parameter in chemical probes.

Andrew McGown^1,2, Jordan Nafie³, Mohammed Otayfah¹

¹Department of Chemistry, School of Life Sciences, University of Sussex Falmer BN1 9QJ UK g.kostakis@sussex.ac.uk j.spencer@sussex.ac.uk.

RSC Chemical Biology

|October 6, 2023

Summary

This summary is machine-generated.

Incorrect chirality assignment in chiral building blocks leads to significant research and development issues. Enhanced supplier control and end-user verification of chirality are crucial for reliable drug development.

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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

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Area of Science:

Organic Chemistry
Medicinal Chemistry
Chemical Manufacturing

Background:

Many pharmaceuticals and bioactive molecules are chiral, necessitating the use of chiral building blocks in synthesis.
Incorrect assignment of chirality by manufacturers can lead to substantial problems for end-users, including irreproducibility and increased costs.

Discussion:

The consequences of misassigned chirality range from experimental failures and wasted resources to serious safety and ethical concerns, particularly with in vivo drug administration.
Implementing stringent chirality control by suppliers and verification by end-users is essential to mitigate these risks.

Key Insights:

Certification of chirality provides confidence in chemical structure assignment.
Techniques such as polarimetry, chiral HPLC, vibrational circular dichroism, and X-ray crystallography can be used for chirality verification.
Case studies highlight the practical implications of incorrect chirality assignment.

Outlook:

Adoption of robust chirality certification processes will enhance the reliability of chemical synthesis and drug development.
Proactive measures by suppliers and end-users can prevent significant financial and reputational damage.
Ensuring stereoisomeric purity is paramount for drug safety and efficacy.