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 |
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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 |