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Related Concept Videos

X-ray Diffraction of Biological Samples01:10

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X-ray diffraction or XRD is an analytical tool that utilizes X-rays to study ordered structures such as crystalline organic and inorganic samples, polycrystalline materials, proteins, carbohydrates, and drugs.
According to Bragg's law, when X-rays strike the sample positioned on a stage, the rays are  scattered by the electron clouds around the sample atoms. The  X-ray diffraction or scattering is caused by constructive interference of the X-ray waves that reflect off the internal...
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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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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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At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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Fully Autonomous Characterization and Data Collection from Crystals of Biological Macromolecules
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Polymorphism in oxyresveratrol studied by 3D ED.

Elena Husanu1, Vincentia Emerson Agbemeh1,2, Iryna Andrusenko1

  • 1Electron Crystallography, Center for Material Interfaces, Istituto Italiano di Tecnologia, Viale Rinaldo Piaggio 34, Pontedera 56025, Italy.

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|October 14, 2024
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Summary
This summary is machine-generated.

Researchers discovered new crystal structures of oxyresveratrol, a natural compound used in Asian medicine. Advanced techniques like 3D electron diffraction revealed previously unknown anhydrate and dihydrate forms, enhancing our understanding of this important botanical extract.

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Area of Science:

  • Crystallography and solid-state chemistry.
  • Natural product chemistry and structural elucidation.
  • Advanced materials characterization.

Background:

  • Oxyresveratrol is a natural polyphenol with traditional medicinal uses in Asia.
  • Understanding the solid-state forms (polymorphism) is crucial for its pharmaceutical applications.
  • Previous studies have not fully characterized the polymorphic landscape of oxyresveratrol.

Purpose of the Study:

  • To investigate the polymorphism of oxyresveratrol using cutting-edge techniques.
  • To identify and structurally characterize novel crystalline forms of oxyresveratrol.
  • To elucidate the thermal behavior and conformational stability of oxyresveratrol polymorphs.

Main Methods:

  • 3D electron diffraction (3D ED) for submicrometric crystal structure determination.
  • Cryo-plunging and routine solid-state analysis.
  • Thermal analysis (DSC/TGA) and Differential Scanning Calorimetry (DSC).
  • Density Functional Theory (DFT) calculations for conformational analysis.

Main Results:

  • A novel anhydrate crystal structure of oxyresveratrol was identified for the first time.
  • A new polymorph of the dihydrate form of oxyresveratrol was discovered and characterized.
  • Thermal studies detailed the dehydration pathways and stability of the identified forms.
  • DFT calculations provided insights into the stability of hydrated conformers.

Conclusions:

  • 3D electron diffraction is a powerful tool for characterizing nanocrystalline natural products.
  • The study expands the known polymorphic forms of oxyresveratrol.
  • This research provides a foundation for controlling and utilizing specific oxyresveratrol solid forms in applications.