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Related Concept Videos

Chirality02:25

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...
Molecules with Multiple Chiral Centers02:25

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 Sulfur02:30

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...
Prochirality02:05

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 Nature02:30

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...
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

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...

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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
08:51

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

Chiral toxicology: it's the same thing...only different.

Silas W Smith1

  • 1New York University School of Medicine, New York, New York 10016, USA. Silas.Smith@nyumc.org

Toxicological Sciences : an Official Journal of the Society of Toxicology
|May 6, 2009
PubMed
Summary

Chirality significantly impacts drug development, metabolism, and toxicity due to differing stereoisomer properties. Understanding these chiral differences is crucial for effective and safe therapeutic and forensic applications.

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A Convenient Method for Extraction and Analysis with High-Pressure Liquid Chromatography of Catecholamine Neurotransmitters and Their Metabolites
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A Micropatterning Assay for Measuring Cell Chirality
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A Micropatterning Assay for Measuring Cell Chirality

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A Convenient Method for Extraction and Analysis with High-Pressure Liquid Chromatography of Catecholamine Neurotransmitters and Their Metabolites
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A Micropatterning Assay for Measuring Cell Chirality
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A Micropatterning Assay for Measuring Cell Chirality

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Area of Science:

  • Pharmacology
  • Toxicology
  • Organic Chemistry

Background:

  • Chiral substances exhibit non-superimposable mirror images (enantiomers) with potentially distinct biological activities.
  • Living systems often display stereospecific interactions, making enantiomer properties critical for physiological effects.
  • Racemic mixtures and individual stereoisomers can have significantly different physicochemical and biochemical properties.

Purpose of the Study:

  • To highlight the importance of chirality in drug development, pharmacokinetics, pharmacodynamics, and toxicity.
  • To discuss the implications of stereoselective metabolism and in vivo racemization of chiral drugs.
  • To illustrate the role of chiral analysis in environmental toxicology, forensic science, and clinical toxicology.

Main Methods:

  • Review of scientific literature on chiral compounds and their biological effects.
  • Discussion of specific examples of chiral drugs, environmental toxins, and forensic analytes.
  • Exploration of structure-activity relationships and stereoselective processes.

Main Results:

  • Enantiomeric selection in drug development can enhance efficacy or reduce toxicity, but challenges remain.
  • Stereoselective metabolism and in vivo racemization can alter drug behavior and outcomes.
  • Chiral dependence is observed in bioaccumulation, persistence, and toxicity of environmental compounds.
  • Chiral analysis aids in forensic investigations, including illicit drug identification and doping control.

Conclusions:

  • Chirality is a fundamental consideration in pharmacology, toxicology, and forensic science.
  • Understanding enantiomer-specific properties is essential for optimizing drug therapy and minimizing adverse events.
  • Chiral toxicology provides critical insights into chemical safety, environmental impact, and legal investigations.