6533b7cffe1ef96bd1258652

RESEARCH PRODUCT

Peptide Metal–Organic Frameworks for Enantioselective Separation of Chiral Drugs

Yolanda Moliner-martínezDmytro AntypovPilar Campíns-falcóMatthew J. RosseinskyCarlos Martí-gastaldoA. Argente-garcíaDaniel Roca-sanjuánJosé Navarro-sánchez

subject

StereoisomerismTripeptideMolecular Dynamics Simulation010402 general chemistry01 natural sciencesBiochemistryCatalysisMethamphetamineColloid and Surface ChemistryOrganic chemistryMoleculeMetal-Organic FrameworksEphedrineMolecular Structure010405 organic chemistryChemistryDiastereomerEnantioselective synthesisStereoisomerismQuímicaGeneral ChemistryCombinatorial chemistry0104 chemical sciences13. Climate actionRacemic mixtureMetal-organic frameworkPèptidsEnantiomerPeptidesMonte Carlo MethodCopper

description

We report the ability of a chiral Cu(II) 3D 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 result of either stronger or additional H-bonds with the framework that lead to energetically more stable diastereomeric adducts. Solid phase extraction (SPE) of a racemic mixture by using Cu(GHG) as extractive phase permits isolating more than 50% of the (+)-ephedrine enantiomer as target compound in only four minutes. To the best of our knowledge, this represents the first example of a MOF capable of separating chiral polar drugs.

https://doi.org/10.1021/jacs.7b00280