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Peptide-based carbohydrate receptors.

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    Cyclic hexapeptides selectively bind carbohydrates in water. Researchers identified stable complexes between specific peptide isomers and sugars like N-acetylneuraminic acid and trehalose.

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    Area of Science:

    • Biochemistry
    • Chemical Biology
    • Structural Biology

    Background:

    • Protein-carbohydrate interactions are crucial for numerous physiological processes.
    • Cyclic hexapeptides have emerged as promising agents for selective carbohydrate recognition.
    • Understanding these noncovalent interactions is key to developing novel therapeutic and diagnostic tools.

    Purpose of the Study:

    • To investigate the noncovalent interactions between two cyclic hexapeptides, HisHis and TyrTyr, and various monosaccharides and disaccharides in aqueous solution.
    • To characterize the binding affinities and structural basis of these peptide-carbohydrate complexes.
    • To confirm experimental findings through computational modeling.

    Main Methods:

    • Synthesis of parallel and antiparallel isomers of HisHis and TyrTyr cyclic hexapeptides.
    • Isothermal titration calorimetry (ITC) to measure binding thermodynamics.
    • NMR spectroscopy titrations to monitor binding events and structural changes.
    • Circular dichroism (CD) spectroscopy to assess conformational changes upon binding.
    • Quantum chemical methods for structure prediction and interaction analysis.

    Main Results:

    • Identified highly stable complexes (Ka > 1000 M⁻¹) between the parallel isomer of HisHis and N-acetylneuraminic acid and methyl-α-D-galactopyranoside.
    • Both parallel and antiparallel isomers of TyrTyr formed stable complexes with trehalose.
    • Computational studies corroborated the experimental observations, predicting multiple intermolecular hydrogen bonds in the most stable complexes.
    • Demonstrated the selectivity of cyclic hexapeptides for specific carbohydrate structures in aqueous environments.

    Conclusions:

    • Cyclic hexapeptides HisHis and TyrTyr exhibit selective and high-affinity binding to specific carbohydrates in water.
    • The observed selectivity is governed by the peptide sequence, isomerism, and the carbohydrate structure.
    • Computational modeling provides valuable insights into the structural basis of these noncovalent interactions.
    • These findings highlight the potential of cyclic peptides as carbohydrate recognition agents.