title: Peptide Metal-Organic Frameworks for Enantioselective Separation of Chiral Drugs.
abstract: We report the use of a chiral Cu(II) 3D metal-organic framework (MOF) based on the tripeptide Gly-l-His-Gly (GHG) for the enantioselective separation of metamphetamine and ephedrine. Monte Carlo simulations suggest that chiral recognition is linked to preferential binding of one of the enantiomers as a result of either stronger or additional H-bonds with the framework that lead to energetically more stable diastereomeric adducts. Solid-phase extraction of a racemic mixture by using Cu(GHG) as the extractive phase permits isolating >50% of the (+)-ephedrine enantiomer as target compound in only 4 min. To our knowledge, this represents the first example of a MOF capable of separating chiral polar drugs.
authors.affiliation: Instituto de Ciencia Molecular, Universidad de Valencia , 46980 Paterna, Spain.
authors.forename: José
authors.initials: J
authors.lastname: Navarro-Sánchez
authors.affiliation: MINTOTA Research Group, Departament de Química Analítica, Facultat de Química, Universitat de Valencia , 46100 Burjassot, Spain.
authors.forename: Ana I
authors.initials: AI
authors.lastname: Argente-García
authors.affiliation: MINTOTA Research Group, Departament de Química Analítica, Facultat de Química, Universitat de Valencia , 46100 Burjassot, Spain.
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Moliner-Martínez
authors.affiliation: Instituto de Ciencia Molecular, Universidad de Valencia , 46980 Paterna, Spain.
authors.forename: Daniel
authors.initials: D
authors.lastname: Roca-Sanjuán
authors.affiliation: Department of Chemistry, University of Liverpool , Liverpool L697ZD, U.K.
authors.forename: Dmytro
authors.initials: D
authors.lastname: Antypov
authors.affiliation: MINTOTA Research Group, Departament de Química Analítica, Facultat de Química, Universitat de Valencia , 46100 Burjassot, Spain.
authors.forename: Pilar
authors.identifier: 0000-0002-0980-8298
authors.initials: P
authors.lastname: Campíns-Falcó
authors.affiliation: Department of Chemistry, University of Liverpool , Liverpool L697ZD, U.K.
authors.forename: Matthew J
authors.identifier: 0000-0002-1910-2483
authors.initials: MJ
authors.lastname: Rosseinsky
authors.affiliation: Instituto de Ciencia Molecular, Universidad de Valencia , 46980 Paterna, Spain.
authors.forename: Carlos
authors.identifier: 0000-0003-3203-0047
authors.initials: C
authors.lastname: Martí-Gastaldo
mesh_terms: D003300:Copper / Q000737:chemistry*; D004809:Ephedrine / Q000737:chemistry / Q000302:isolation & purification*; D000073396:Metal-Organic Frameworks / Q000737:chemistry*; D008694:Methamphetamine / Q000737:chemistry / Q000302:isolation & purification*; D056004:Molecular Dynamics Simulation; D015394:Molecular Structure; D009010:Monte Carlo Method; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000073396:Metal-Organic Frameworks; D010455:Peptides; D008694:Methamphetamine; D003300:Copper; D004809:Ephedrine