Peptide Metal-Organic Frameworks for Enantioselective Separation of Chiral Drugs



Navarro-Sanchez, Jose, Argente-Garcia, Ana I, Moliner-Martinez, Yolanda, Roca-Sanjuan, Daniel, Antypov, Dmytro ORCID: 0000-0003-1893-7785, Campins-Falco, Pilar, Rosseinsky, Matthew J ORCID: 0000-0002-1910-2483 and Marti-Gastaldo, Carlos
(2017) Peptide Metal-Organic Frameworks for Enantioselective Separation of Chiral Drugs. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 139 (12). pp. 4294-4297.

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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.

Item Type: Article
Uncontrolled Keywords: Copper, Ephedrine, Methamphetamine, Peptides, Monte Carlo Method, Molecular Structure, Stereoisomerism, Molecular Dynamics Simulation, Metal-Organic Frameworks
Depositing User: Symplectic Admin
Date Deposited: 30 Mar 2017 09:49
Last Modified: 19 Jan 2023 07:07
DOI: 10.1021/jacs.7b00280
Open Access URL: http://pubs.acs.org/doi/abs/10.1021/jacs.7b00280
Related URLs:
URI: https://livrepository.liverpool.ac.uk/id/eprint/3006722