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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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On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to...
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Radical Halogenation: Stereochemistry01:33

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Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

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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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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Naming Enantiomers02:21

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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...
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Related Experiment Video

Updated: Jun 17, 2025

Microcrystal Electron Diffraction of Small Molecules
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Microcrystal Electron Diffraction of Small Molecules

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Structural Elucidation and Absolute Stereochemistry for Pharma Compounds Using MicroED.

Lygia Silva de Moraes1, Jessica E Burch1,2,3, David A Delgadillo1

  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Organic Letters
|August 8, 2024
PubMed
Summary
This summary is machine-generated.

Microcrystal electron diffraction (microED) rapidly analyzes small crystals of pharmaceutical compounds. This method accurately determined absolute stereochemistry, proving valuable for drug discovery.

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Area of Science:

  • Crystallography
  • Electron Diffraction
  • Drug Discovery

Background:

  • Microcrystal electron diffraction (microED) is a rapidly developing technique for analyzing micro- and nanocrystals.
  • Its application to pharmaceutical compounds is an area of active investigation.

Purpose of the Study:

  • To evaluate the utility of microED for the crystallographic analysis of pharmaceutical compounds.
  • To assess the capability of microED in determining the absolute stereochemistry of chiral drug molecules.

Main Methods:

  • Analysis of 30 diverse pharmaceutical samples using microcrystal electron diffraction (microED).
  • Structure elucidation of micro- and nanocrystals obtained from process and medicinal chemistry groups.
  • Application of dynamical refinement to continuous rotation electron diffraction data for stereochemistry assignment.

Main Results:

  • 15 out of 30 crystal structures were successfully elucidated within 40 hours of microscope time.
  • The absolute stereochemistry of all chiral compounds was correctly assigned using dynamical refinement.
  • MicroED proved effective for rapid structure determination of pharmaceutical compounds.

Conclusions:

  • Microcrystal electron diffraction (microED) is a highly applicable technique for the rapid analysis of pharmaceutical compounds.
  • Dynamical refinement of microED data is a reliable method for determining the absolute stereochemistry of chiral drug candidates.
  • This technique holds significant promise for accelerating drug discovery and development processes.