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Related Concept Videos

Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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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...
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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Chirality02:25

Chirality

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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...
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Prochirality02:05

Prochirality

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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...
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Chirality in Nature02:30

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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.
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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.
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Updated: Sep 15, 2025

A Micropatterning Assay for Measuring Cell Chirality
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Chiral medium-sized rings beyond central chirality.

Shiqi Jia1, Yudong Hao2, Yuedi Li2

  • 1Department of Chemistry, Zhengzhou University, Zhengzhou, China. jiashiqi17@zzu.edu.cn.

Nature Reviews. Chemistry
|July 14, 2025
PubMed
Summary
This summary is machine-generated.

This review explores unconventional chirality in medium-sized rings (MSRs), focusing on axial, inherent, and planar types. It details synthetic strategies and conformational stability factors for these important bioactive molecules.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Stereochemistry

Background:

  • Medium-sized rings (MSRs) are crucial structural motifs in many bioactive molecules.
  • While central chirality in MSRs is well-studied, unconventional chiral types remain underexplored.
  • Unconventional chirality includes axial, inherent, and planar chirality.

Purpose of the Study:

  • To review recent advances in the synthesis of MSRs with unconventional chirality.
  • To critically evaluate the advantages and limitations of various synthetic strategies.
  • To discuss factors influencing the conformational stability of chiral MSRs.

Main Methods:

  • Literature review of synthetic methodologies for chiral MSRs.
  • Analysis of structure and energy to understand conformational stability.
  • Critical evaluation of synthetic routes and their applicability.

Main Results:

  • Significant progress has been made in synthesizing MSRs with axial, inherent, and planar chirality over the past decade.
  • Key synthetic strategies for each type of unconventional chirality have been identified.
  • Factors affecting conformational stability, such as ring size and substitution patterns, have been elucidated.

Conclusions:

  • Chiral MSRs with unconventional chirality represent a promising area for drug discovery.
  • Further research into their synthesis and conformational properties will unlock new applications.
  • This review provides a comprehensive overview for researchers in the field.