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Anomeric Effects in Sulfamides.

Eric Hansen1, Elaine Limé2, Per-Ola Norrby2

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This summary is machine-generated.

Sulfamides and sulfonamides possess unique electronic structures crucial for biological activity. This study reveals these properties stem from a coupled double anomeric effect, enabling accurate force field parameterization for molecular mechanics.

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Area of Science:

  • Computational chemistry
  • Medicinal chemistry
  • Molecular modeling

Background:

  • Sulfamides and sulfonamides are prevalent functional groups in biologically active compounds.
  • Their activity is linked to mimicking tetrahedral intermediates of enzymes like proteases and esterases.
  • Understanding their unique electronic and conformational properties is key.

Purpose of the Study:

  • To analyze the origin of unique structural elements in sulfamides and sulfonamides.
  • To investigate the role of coupled, double anomeric effects.
  • To develop accurate force field parameters for molecular mechanics simulations.

Main Methods:

  • Density Functional Theory (DFT) calculations
  • Conformational scans
  • Natural Bond Orbital (NBO) analysis
  • Quantum-guided molecular mechanics (Q2MM) method

Main Results:

  • The unique structural features are attributed to a coupled, double anomeric effect.
  • DFT and NBO analyses elucidated the electronic origins.
  • Q2MM successfully parametrized MM3* force fields for sulfamides and sulfonamides.

Conclusions:

  • The coupled double anomeric effect explains the conformational behavior of sulfamides/sulfonamides.
  • Accurate force field parameters were derived using Q2MM.
  • This facilitates advanced molecular mechanics studies of these important compound classes.