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Enantioselective molecular recognition between beta-sheets.

De Michael Chung1, James S Nowick

  • 1Department of Chemistry, University of California, Irvine, California 92697-2025, USA.

Journal of the American Chemical Society
|March 12, 2004
PubMed
Summary
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Homochiral beta-sheet pairing is strongly preferred over heterochiral pairing between enantiomeric beta-sheets. This preference in molecular recognition is driven by favorable interactions in homochiral structures.

Area of Science:

  • Biochemistry
  • Molecular Biology
  • Structural Chemistry

Background:

  • Protein structure and function rely on beta-sheet interactions.
  • Beta-sheets can form homochiral (l-l or d-d) or heterochiral (l-d) pairings.
  • Understanding these interactions is key to protein folding and molecular recognition.

Purpose of the Study:

  • To determine the preferred interaction between enantiomeric beta-sheets (l-beta-sheets and d-beta-sheets).
  • To quantify the selectivity for homochiral versus heterochiral beta-sheet dimerization.

Main Methods:

  • Synthesis of l-beta-sheets (1a-d) and d-beta-sheets (2a-c) composed of enantiomeric amino acids.
  • 1H Nuclear Magnetic Resonance (NMR) spectroscopy to analyze dimer formation in organic solvents.

Related Experiment Videos

  • Quantification of homochiral and heterochiral dimer ratios and calculation of free-energy differences.

    • Main Results:

    • Homochiral beta-sheet dimers strongly predominated over heterochiral dimers when l-beta-sheets were mixed with d-beta-sheets.
    • Measured ratios of homochiral to heterochiral dimers ranged from 95.8:4.2 to 98.5:1.5.
    • Statistically corrected free-energy differences indicated a significant preference for homochiral pairing (3.1-4.2 kcal/mol).

    Conclusions:

    • Molecular recognition between enantiomeric beta-sheets exhibits high enantioselectivity, favoring homochiral interactions.
    • Favorable nonbonded contacts in homochiral structures and steric clashes in heterochiral structures likely explain this preference.
    • Findings provide insights into the principles governing self-assembly and molecular recognition in chiral systems.