title: Synergistic effects of trace amounts of water in the enantiodiscrimination processes by lipodex E: a spectroscopic and computational investigation.
abstract: Nuclear magnetic resonance (NMR) investigations on mixtures containing octakis(3-O-butanoyl-2,6-di-O-pentyl)-γ-cyclodextrin (Lipodex E) and each enantiomer of methyl-2-chloropropionate (MCP) ascertained the role of trace amounts of water in the enantiodiscrimination processes. Water is deeply included into the cyclodextrin and favors the formation of the inclusion complex with (S)-MCP, whereas (R)-MCP is only slightly affected, thus causing a significant increase of NMR differentiation. Molecular dynamics simulations were performed to shed light on the possible behavior of Lipodex E in different conditions (i.e., solvent, inclusion complexes), providing energetic and atomistic details that are in agreement with NMR observations.
authors.affiliation: Department of Chemistry and Industrial Chemistry, University of Pisa, Pisa, Italy.
authors.forename: Gloria
authors.initials: G
authors.lastname: Uccello-Barretta
authors.forename: Volker
authors.initials: V
authors.lastname: Schurig
authors.forename: Federica
authors.initials: F
authors.lastname: Balzano
authors.forename: Letizia
authors.initials: L
authors.lastname: Vanni
authors.forename: Federica
authors.initials: F
authors.lastname: Aiello
authors.forename: Mattia
authors.initials: M
authors.lastname: Mori
authors.forename: Francesca
authors.initials: F
authors.lastname: Ghirga
mesh_terms: D003510:Cyclohexanes / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D056004:Molecular Dynamics Simulation; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water; D047408:gamma-Cyclodextrins / Q000737:chemistry*
chemical_list: D003510:Cyclohexanes; D011422:Propionates; D012997:Solvents; D047408:gamma-Cyclodextrins; C113626:octakis(3-O-butanoyl-2,6-di-O-pentyl)cyclodextrin; D014867:Water; C078127:methyl 2-chloropropionate; C506365:Cyclohexane
keywords: NMR spectroscopy; chirality; cyclodextrins; host-guest systems; molecular dynamics