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Related Concept Videos

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

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

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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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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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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.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
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Revisiting prochirality.

Raymond S Ochs1, Tanaji T Talele1

  • 1Department of Pharmaceutical Sciences, College of Pharmacy and Health Sciences, St. John's University, 8000 Utopia Parkway, Queens, NY, 11439, USA.

Biochimie
|December 22, 2019
PubMed
Summary
This summary is machine-generated.

We introduce the prochiral plane model to explain how enzymes create enantiomerically pure products from prochiral substrates. This model redefines understanding of enzyme catalysis and substrate binding, applicable from simple molecules to complex reactions.

Keywords:
AconitaseFumaraseMolecular modelingProchiral planeStereospecificity

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Enzymology

Background:

  • The concept of prochirality is crucial for understanding stereoselective synthesis in biological systems.
  • Existing models like the 'three point attachment' hypothesis have limitations in explaining all observed stereochemical outcomes.
  • A unified and comprehensive model for prochirality is needed to advance the study of enzyme mechanisms.

Purpose of the Study:

  • To propose a novel model, the prochiral plane, to unify the understanding of prochirality in chemical and enzymatic reactions.
  • To demonstrate the applicability of the prochiral plane model to enzyme catalysis, offering an alternative to existing hypotheses.
  • To identify the true prochiral substrate in specific enzymatic reactions and clarify the role of substrate-enzyme interactions.

Main Methods:

  • Development of the prochiral plane model based on geometric principles.
  • Application of the model to known enzymatic reactions, including aconitase and fumarase.
  • Utilizing molecular modeling and analysis of enzymatic mechanisms.
  • Conducting a literature survey of various prochiral substrates.

Main Results:

  • The prochiral plane model successfully explains all known examples of prochirality, including those with sp2 and sp3 hybridized prochiral carbons.
  • The model identifies cis-aconitate, not citrate, as the prochiral substrate for aconitase.
  • Fumarase and fumarate serve as examples demonstrating the prochiral plane concept even with limited binding sites.
  • The model is applicable to both natural and unnatural substrates, such as fingolimod.

Conclusions:

  • The prochiral plane model provides a robust framework for understanding stereoselectivity in enzymatic reactions.
  • Enzyme asymmetry dictates the exclusive delivery of reactants to one face of the prochiral plane, ensuring enantiopurity.
  • The number of substrate-enzyme interaction points is relevant for specificity, not for defining prochirality itself.