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Molecules with Multiple Chiral Centers02:25

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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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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.
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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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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 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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Multiscale chiral zeros in biomolecules.

Neel Moudgal1,2, Jessica Ma2,3, Emine Sumeyra Turali Emre2,3,4

  • 1Department of Biophysics, University of Michigan, Ann Arbor, USA.

Communications Chemistry
|November 26, 2025
PubMed
Summary
This summary is machine-generated.

The Osipov-Pickup-Dunmur (OPD) index has theoretical "chiral zeros," but we found them prevalent in biological molecules. This suggests OPD is unsuitable for quantifying molecular chirality, necessitating new mathematical methods.

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Area of Science:

  • Biochemistry
  • Structural Biology
  • Mathematical Chemistry

Background:

  • Chirality, or mirror asymmetry, is crucial for biomolecular interactions.
  • Quantifying molecular chirality accurately remains a challenge, limiting understanding of its biological roles.
  • Existing measures like the Osipov-Pickup-Dunmur (OPD) index and Hausdorff Chirality Measure (HCM) have limitations.

Purpose of the Study:

  • To investigate the prevalence and implications of theoretical
  • chiral zeros
  • in the Osipov-Pickup-Dunmur (OPD) index within biological systems.
  • To compare the effectiveness of the OPD index and the Hausdorff Chirality Measure (HCM) in quantifying molecular chirality.
  • To highlight the need for improved mathematical approaches for chirality assessment in complex biomolecules.

Main Methods:

  • Analysis of four diverse biological systems to represent various scales of chirality.
  • Evaluation of the Osipov-Pickup-Dunmur (OPD) index for its theoretical
  • chiral zero
  • phenomenon.
  • Comparison of OPD index results with the Hausdorff Chirality Measure (HCM).
  • Assessment of the correlation between chirality measures and biological properties.

Main Results:

  • The study found
  • chiral zeros
  • to be prevalent in the examined biological systems, contradicting theoretical expectations of rarity.
  • The Osipov-Pickup-Dunmur (OPD) index was deemed unsuitable for complex molecular structures, except for simple helicoids.
  • The Hausdorff Chirality Measure (HCM) showed a weak correlation with biological properties.
  • Significant differences were observed between OPD and HCM across various biological scales.

Conclusions:

  • The Osipov-Pickup-Dunmur (OPD) index is unreliable for quantifying the chirality of complex biomolecules due to prevalent
  • chiral zeros
  • .
  • Current chirality measures, including HCM, have limitations in reflecting biological significance.
  • There is a critical need for novel mathematical frameworks to accurately differentiate chiral structures, especially for AI and machine learning applications in structural biology.