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Related Experiment Video

Updated: May 27, 2026

Radiosynthesis of 1-(2-[18F]Fluoroethyl)-L-Tryptophan using a One-pot, Two-step Protocol
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4-Nitro-N-phthalyl-l-tryptophan.

Anaelle Tilborg, Irving Boittiaux, Bernadette Norberg

    Acta Crystallographica. Section E, Structure Reports Online
    |November 18, 2011
    PubMed
    Summary

    This study details the crystal structure of a novel compound, an analogue of epigenetic modulator RG108. Its structure is stabilized by hydrogen bonds and pi-pi stacking interactions between indole and phthalimide rings.

    Area of Science:

    • Crystallography
    • Structural Chemistry
    • Molecular Biology

    Background:

    • Epigenetic modifications play a crucial role in gene regulation.
    • RG108 is a known epigenetic modulator influencing DNA methylation.
    • Understanding the structural basis of such modulators is key to developing new therapeutic agents.

    Purpose of the Study:

    • To elucidate the crystal structure of a novel analogue of the epigenetic modulator RG108.
    • To identify the intermolecular interactions stabilizing the crystal lattice.
    • To provide insights into the structure-activity relationship of RG108 analogues.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.
    • Analysis of hydrogen bonding and π-π stacking interactions was performed.

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  • The crystal structure was compared to known epigenetic modulators.
  • Main Results:

    • The crystal structure of (2R)-3-(1H-indol-3-yl)-2-(4-nitro-1,3-dioxoisoindolin-2-yl)propanoic acid (C19H13N3O6) was determined.
    • Strong intermolecular hydrogen bonds were observed between the indole N-H and phthalimide carbonyl oxygen, and between the carboxyl group and phthalimide carbonyl oxygen.
    • Significant π-π stacking interactions between indole and phthalimide rings were identified with centroid-centroid distances of 3.638(1) and 3.610(1) Å.

    Conclusions:

    • The crystal structure reveals specific hydrogen bonding and π-π stacking interactions that dictate the compound's conformation.
    • These interactions are crucial for the molecular recognition and potential biological activity of this RG108 analogue.
    • The findings contribute to the understanding of epigenetic modulator structures and inform future drug design.