Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Molecular Modeling of Enantio-discrimination of α-Methoxy-α-trifluoromethylphenylacetic Acid (MTPA) by Cyclomaltoheptaose (β-Cyclodextrin) and 6-Amino-6-deoxy-cyclomaltoheptaose

  • Jung, Eun-Kyoung (Department of Microbial Engineering, Kunkuk University) ;
  • Jeong, Karp-Joo (College of Information and Communication and Bio/Molecular Informatics Center, Kunkuk University) ;
  • Lee, Sang-San (Supercomputing Center in Korea Institute of Science and Technology Information) ;
  • Kim, Jee-In (College of Information and Communication and Bio/Molecular Informatics Center, Kunkuk University) ;
  • Jung, Seun-Ho (Department of Microbial Engineering, Kunkuk University)
  • Published : 2003.11.20
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Abstract

Molecular modeling was performed to comprehend the chiral recognition of ${\alpha}$-methoxy-${\alpha}$-trifluoromethylphenylacetic acid (MTPA) enantiomers by cyclomaltoheptaose (${\beta}$-cyclodextrin,${\beta}$-CD) and 6-amino-6-deoxy-cyclomaltoheptaose (am-${\beta}$-CD). Monte Carlo (MC) docking coupled to constant temperature molecular dynamics (MD) simulations was applied to the investigation for the ${\alpha}$-methoxy-${\alpha}$-trifluoromethylphenylacetic acid complexation with two different CDs in terms of the relative distribution of the interaction energies. The calculated results are finely correlated with the experimental observations in chiral recognition thermodynamics. Am-${\beta}$-CD as a host showed the superior enantio-discrimination ability to the native ${\beta}$-CD where the amino group of am-${\beta}$-CD was critically involved in enhancing the ability of chiral discrimination via the Coulombic interaction with MTPA.

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References

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