Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Molecular Modeling of the Chiral Recognition of Propranolol Enantiomers by a β-Cyclodextrin

  • Kim, Hyun-myung (Department of Microbial Engineering and Bio/Molecular Informatics Center, Konkuk University) ;
  • Jeong, Karp-joo (College of Information and Communication,Konkuk University) ;
  • Lee, Sang-san (Supercomputing Center in Korea Institute of Science and Technology Information) ;
  • Jung, Seun-ho (Department of Microbial Engineering and Bio/Molecular Informatics Center, Konkuk University)
  • Published : 2003.01.20
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Abstract

Enantioselectivity of the propranolol on β-cyclodextrin was simulated by molecular modeling. Monte Carlo (MC) docking and molecular dynamics (MD) simulations were applied to investigate the molecular mechanism of enantioselective difference of both enantiomeric complexes. An energetic analysis of MC docking simulations coupled to the MD simulations successfully explains the experimental elution order of propranolol enantiomers. Molecular dynamics simulations indicate that average energy difference between the enantiomeric complexes, frequently used as a measure of chiral recognition, depends on the length of the simulation time. We found that, only in case of much longer MD simulations, noticeable chiral separation was observed.

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