title: A Molecular Dynamics Simulation Study of the Association of 1,1'-Binaphthyl-2,2'-diyl hydrogenphosphate Enantiomers with a Chiral Molecular Micelle.
abstract: Molecular dynamics (MD) simulations were used to investigate the binding of 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate (BNP) enantiomers to the molecular micelle poly-(sodium undecyl-(L,L)-leucine-valine) (poly(SULV)). Poly(SULV) is used as a chiral selector in capillary electrophoresis separations. Four poly(SULV) binding pockets were identified and either (R)-BNP or (S)-BNP were docked into each pocket. MD simulations were then used to identify the preferred BNP binding site. Within the preferred site, both enantiomers formed hydrogen bonds with poly(SULV) and penetrated into the poly(SULV) core. Comparisons of BNP enantiomer binding to the preferred poly(SULV) pocket showed that (S)-BNP formed stronger hydrogen bonds, moved deeper into the binding site, and had a lower poly(SULV) binding free energy than the (R) enantiomer. Finally, MD simulation results were in agreement with capillary electrophoresis and NMR experiments. Each technique showed (S)-BNP interacted more strongly with poly(SULV) than (R)-BNP and that the site of chiral recognition was near the poly(SULV) leucine chiral center.
authors.affiliation: Department of Chemistry, Carthage College, 2001 Alford Park Drive, Kenosha, WI 53140.
authors.forename: Kevin F
authors.initials: KF
authors.lastname: Morris
authors.affiliation: Department of Physical and Environmental Sciences, Texas A&M University-Corpus Christi, 6300 Ocean Drive, Corpus Christi, TX, 78412.
authors.forename: Eugene J
authors.initials: EJ
authors.lastname: Billiot
authors.affiliation: Department of Physical and Environmental Sciences, Texas A&M University-Corpus Christi, 6300 Ocean Drive, Corpus Christi, TX, 78412.
authors.forename: Fereshteh H
authors.initials: FH
authors.lastname: Billiot
authors.affiliation: Department of Chemistry, Carthage College, 2001 Alford Park Drive, Kenosha, WI 53140.
authors.forename: Ashley A
authors.initials: AA
authors.lastname: Gladis
authors.affiliation: Office of Naval Research, 875 North Randolph Street, Arlington, VA 22203-1995.
authors.forename: Kenny B
authors.initials: KB
authors.lastname: Lipkowitz
authors.affiliation: Department of Biochemistry and Molecular Biology, Howard University College of Medicine, Howard University, 520 W Street NW, Washington, DC 20059.
authors.forename: William M
authors.initials: WM
authors.lastname: Southerland
authors.affiliation: Department of Biochemistry and Molecular Biology, Howard University College of Medicine, Howard University, 520 W Street NW, Washington, DC 20059.
authors.forename: Yayin
authors.initials: Y
authors.lastname: Fang
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