Chiral Linker Systems

Kutzscher, Christel; Müller, Philipp; Raschke, Silvia; Kaskel, Stefan

doi:10.1002/9783527693078.ch13

Cited by 5 publications

(6 citation statements)

References 115 publications

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“…However, the application of MOFs in enantioselective separation remains still limited by small number of homochiral, microporous phases available. 5,6 These are typically prepared either by using chiral templates that drive enantiomeric resolution, by post-synthetic linker exchange for partial grafting of chiral linkers in the metal struts at expense of accessible porosity or direct synthesis from enantiopure linkers. 5 This last route is compatible with the use of naturally occurring chiral linkers like camphoric and tartaric acid, amino acids (aa's) or oligopeptides.…”

mentioning

confidence: 99%

“…5,6 These are typically prepared either by using chiral templates that drive enantiomeric resolution, by post-synthetic linker exchange for partial grafting of chiral linkers in the metal struts at expense of accessible porosity or direct synthesis from enantiopure linkers. 5 This last route is compatible with the use of naturally occurring chiral linkers like camphoric and tartaric acid, amino acids (aa's) or oligopeptides. Among these, peptides are well suited to producing functional, chiral MOFs whose robustness, chemical stability and porous response can be effectively modulated by suitable choice of aa's in the peptidic sequence.…”

mentioning

confidence: 99%

“…They can be more easily engineered to deploy a periodic array of chiral channels that are accessible to guest sorption and can be modified in size, shape, and chemical function to optimize mass-transfer rates and chiral recognition. However, the application of MOFs in enantioselective separation is still limited by the small number of homochiral, microporous phases available . These are typically prepared either by using chiral templates that drive enantiomeric resolution, by postsynthetic linker exchange for partial grafting of chiral linkers in the metal struts at the expense of accessible porosity, or by direct synthesis from enantiopure linkers .…”

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confidence: 99%

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Peptide Metal–Organic Frameworks for Enantioselective Separation of Chiral Drugs

et al. 2017

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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.

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Peptide Metal–Organic Frameworks for Enantioselective Separation of Chiral Drugs

et al. 2017

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“…L-tyrosine, L-histidine, L-tryptophan and L-glutamic acid), 42 diacids (e.g. D-(+)-camphoric acid, tartaric acid and malic acid) 43 and enantiopure carbohydrates (e.g. sugars).…”

Section: Strategies For Synthesizing Hmofs For Asymmetric Catalysismentioning

confidence: 99%

Homochiral metal–organic frameworks as heterogeneous catalysts

Gheorghe

Tepaske

Tanase

2018

Inorg. Chem. Front.

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“…Chiral MOFs from enantiopure organic linkers like camphoric acid, tartaric acid, amino acids, or oligopeptides have been reported and used for chiral separation or asymmetric catalysis . However, these molecules are small and limit the porosity metrics of the resulting frameworks, thereby restricting the size of the guest, mass transfer, analyte concentration, and subsequent interactions with the solid support.…”

Section: Introductionmentioning

confidence: 99%

Homochiral Metal–Organic Frameworks for Enantioselective Separations in Liquid Chromatography

Corella‐Ochoa

Tapia²,

Rubin³

et al. 2019

J. Am. Chem. Soc.

103

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Selective separation of enantiomers is a substantial challenge for the pharmaceutical industry. Chromatography on chiral stationary phases is the standard method, but at a very high cost for industrial-scale purification due to the high cost of the chiral stationary phases. Typically, these materials are poorly robust, expensive to manufacture, and often too specific for a single desired substrate, lacking desirable versatility across different chiral analytes. Here, we disclose a porous, robust homochiral metalorganic framework (MOF), TAMOF-1, built from copper(II) and an affordable linker prepared from natural L-histidine. TAMOF-1 has shown to be able to separate a variety of model racemic mixtures, including drugs, in a wide range of solvents of different polarity, outperforming several commercial chiral columns for HPLC separations. Although not exploited in the present article, it is worthy to mention that the preparation of this new material is scalable to the multikilogram scale, opening unprecedented possibilities for low-energy chiral separation at the industrial scale.

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Chiral Linker Systems

Cited by 5 publications

References 115 publications

Peptide Metal–Organic Frameworks for Enantioselective Separation of Chiral Drugs

Peptide Metal–Organic Frameworks for Enantioselective Separation of Chiral Drugs

Homochiral metal–organic frameworks as heterogeneous catalysts

Homochiral Metal–Organic Frameworks for Enantioselective Separations in Liquid Chromatography

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