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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...

Naming Enantiomers

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...

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...

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. The...

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Related Experiment Video

Updated: Jul 28, 2026

Electrochemiluminescence Assays for Human Islet Autoantibodies

Electrochemiluminescence Assays for Human Islet Autoantibodies

Published on: March 23, 2018

Algorithms for validating chiral properties of insulins.

N Purdie¹, D W Province, T P Layloff

¹Chemistry Department, Oklahoma State University, Stillwater 74078-0447, USA.

Analytical Chemistry

|August 28, 1999

Summary

Chiral ligand exchange with circular dichroism spectropolarimetry offers a fast, simple method to validate peptide and protein chirality. This technique shows promise for automated quality control of biomolecules like insulin.

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Area of Science:

Analytical Chemistry
Biochemistry
Spectroscopy

Background:

Chirality is crucial for peptide and protein function.
Existing methods for chirality validation can be complex or time-consuming.
Need for robust analytical techniques for quality control of biopharmaceuticals.

Purpose of the Study:

To introduce a novel, rapid method for validating peptide and protein chirality.
To demonstrate the applicability of the method using various insulin samples.
To assess the potential for automated quality control.

Main Methods:

Chiral ligand exchange reaction using Cu(II) complexes in aqueous base.
Circular dichroism (CD) spectropolarimetric detection.
Analysis of human, porcine, and bovine insulin samples from diverse sources.

Main Results:

The combined method provides excellent validation of chirality properties.
The procedure is quick and simple to perform.
Demonstrated specificity suitable for various peptide and protein forms.

Conclusions:

The developed method is a powerful tool for assessing peptide and protein chirality.
Potential for integration into automated quality control workflows.
Applicable to a wide range of peptide and protein analytes, including insulin variants.