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Conformational studies on cyclic dipeptides

R Ramani, V Sasisekharan, K Venkatesan

    International Journal of Peptide and Protein Research
    |January 1, 1977
    PubMed
    Summary
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    This study analyzes cyclic dipeptide structures, revealing preferred side-chain conformations and DKP ring possibilities. Theoretical calculations align well with experimental data, validating the models for these important biomolecules.

    Area of Science:

    • Structural chemistry
    • Computational chemistry
    • Biochemistry

    Background:

    • Cyclic dipeptides, also known as diketopiperazines (DKPs), are prevalent in nature and pharmaceuticals.
    • Understanding their conformational preferences is crucial for drug design and understanding biological roles.

    Purpose of the Study:

    • To analyze existing crystal structures of cyclic dipeptides.
    • To investigate preferred side-chain and DKP ring conformations using computational methods.
    • To explore the role of non-bonded interactions in conformational changes.

    Main Methods:

    • Analysis of 11 reported crystal structures of cyclic dipeptides.
    • Classical energy calculations for preferred side-chain conformations.
    • Conformational analysis of the diketopiperazine (DKP) ring.

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  • Investigation of non-bonded interactions influencing conformational pathways.

    • Main Results:

    • Identified preferred conformations for side chains of cyclic dipeptides with various alpha-amino acid residues.
    • Determined possible conformations of the DKP ring.
    • Demonstrated the significance of non-bonded interactions in dictating conformational changes.
    • Achieved good agreement between theoretical predictions and experimental observations (NMR studies).

    Conclusions:

    • Theoretical models accurately predict cyclic dipeptide conformations and conformational enthalpy differences.
    • The study provides valuable insights into the structural and energetic properties of cyclic dipeptides.
    • Findings support the use of computational methods for predicting DKP behavior.