Determination of Enantiomeric Excess by Solid-Phase Extraction Using a Chiral Metal-Organic Framework as Sorbent

Zhang, Junhui; Tang, Bo; Wang, Bang-Jin; Zhang, Mei; Chen, Xinglian; Zi, Min

doi:10.3390/molecules23112802

Cited by 8 publications

(7 citation statements)

References 41 publications

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“…152 A new MOF [Co(L-tyr)] n (L-tyrCo) was synthesized and utilized as a sorbent to determine ee of (±)-1,1 0 -bi-2-naphthol using SPE. 163 [Zn 2 (D-Cam) 2 (4,4 0 -bpy)] n and [Co(Ltyr)] n (L-tyrCo) MOFs showed good accuracy and promising results for determination of ee of chiral compounds. 152,163 A chiral Cu-II 3D-MOF-based on tripeptide Gly-L-His-Gly (GHG) was developed for chiral selective separation of ephedrine and methamphetamine.…”

Section: Magnetic Mof In Spementioning

confidence: 99%

“…163 [Zn 2 (D-Cam) 2 (4,4 0 -bpy)] n and [Co(Ltyr)] n (L-tyrCo) MOFs showed good accuracy and promising results for determination of ee of chiral compounds. 152,163 A chiral Cu-II 3D-MOF-based on tripeptide Gly-L-His-Gly (GHG) was developed for chiral selective separation of ephedrine and methamphetamine. The developed MOF [Cu (GHG)] was used as sorbent in SPE and isolated 50% of (+)-ephedrine enantiomer in 4 min from a racemic mixture.…”

Section: Magnetic Mof In Spementioning

confidence: 99%

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Metal–organic frameworks in chiral separation of pharmaceuticals

et al. 2022

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Stereoselective chiral molecules are responsible for specific biological functions in nature. At present, more than half of the prescribed drugs are chiral. Living organisms display divergent pharmacological responses to the enantiomers, leading to altered toxicity, pharmacokinetics, and pharmacodynamics. Thus, chiral analysis, separation, and extraction are crucial for ensuring enantiomeric purity to develop safe and effective medication. In recent times, metal–organic frameworks (MOFs) with appealing structures are gaining importance because of their fascinating properties as a sorbent and stationary phase. MOFs are crystalline porous solid materials built by interconnecting metal ions or clusters and organic linkers. This review explores the advancements in MOFs for the isolation and separation of chiral active pharmaceutical drugs.

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Section: Magnetic Mof In Spementioning

confidence: 99%

Section: Magnetic Mof In Spementioning

confidence: 99%

Metal–organic frameworks in chiral separation of pharmaceuticals

et al. 2022

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“…Chirality is a fundamental property of nature. Enantiomers of chiral drugs always have significant different pharmacological activities in the treatment of diseases 1,2 . So numerous efforts have been made to obtain optically pure enantiomers in the past decades 3–9 .…”

Section: Introductionmentioning

confidence: 99%

“…Enantiomers of chiral drugs always have significant different pharmacological activities in the treatment of diseases. 1,2 So numerous efforts have been made to obtain optically pure enantiomers in the past decades. [3][4][5][6][7][8][9] Chiral extraction is a promising method to separate optically pure enantiomer which has the advantages of simple process, low cost, and high recovery.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of amino acid and mandelic acid enantiomers using Garphos derivatives as chiral extractants

Wang

Yang²,

Chen

et al. 2022

Chirality

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In this paper, Garphos with different substituents were employed as chiral extractants to enantioseparate racemic amino acid and mandelic acid. The influences of metal precursors, pH of aqueous solution, Garphos-metal concentration, extraction temperature, and substituent effect on extraction were investigated. The results indicated that the substituent groups significantly affected the π-π interaction between extractant and substrate. And the separation factors (α) for Garphos could be remarkably improved by regulating substituent groups. Garphos-II-Pd, Garphos-VI-Pd, Garphos-III-Pd, Garphos-I-Cu, Garphos-VI-Cu, and Garphos-V-Pd were the most efficient extractants for phenylalanine (Phe), homophenylalanine (Hphe), 4-nitrophenylalanine (Nphe), 3-chlorophenylglycine (Cpheg), mandelic acid (MA), and 2-chlormandelic acid (CMA) with α values of 2. 40, 2.37, 5.37, 1.59, 5.98, and 3.69, respectively. This work provided an important reference for the design of efficient chiral extractants in future work.

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“…In general, one enantiomer of chiral drugs is safe and effective, while the other is maybe ineffective or even toxic. 1 There are many examples of chiral medicines whose enantiomers vary drastically in their properties. For instance, the antimicrobial activity of (S)-ofloxacin is 9.3 times that of (R)-ofloxacin.…”

Section: Introductionmentioning

confidence: 99%

Investigation of Taniaphos as a chiral selector in chiral extraction of amino acid enantiomers

et al. 2021

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Finding chiral selector with high stereoselectivity to a variety of amino acid enantiomers remains a challenge and warrants further research. In this work, Taniaphos, a chiral ligand with rotatable spatial configuration, was employed as a chiral extractant to enantioseparate various amino acid enantiomers. Phenylalanine (Phe), homophenylalanine (Hphe), 4-nitrophenylalanine (Nphe), and 3-chloro-phenylglycine (Cpheg) were used as substrates to evaluate the extraction efficiency. The results revealed that Taniaphos-Cu exhibited good abilities to enantioseparate Phe, Hphe, Nphe, and Cpheg with the highest separation factors (α) of 3.13, 2.10, 2.32, and 2.14, respectively. Taniaphos-Cu is more conducive to combine with D-amino acid in extraction. The influences of pH, Taniaphos-Cu, and concentration and extraction temperature on extraction were comprehensively evaluated. The highest performance factors (pf ) for Phe, Hphe, Nphe, and Cpheg at optimal extraction conditions were 0.08892, 0.1250, 0.09621, and 0.08021, respectively. The recognition mechanism between Taniaphos-Cu and amino acid enantiomers was discussed. The coordination interaction between Taniaphos-Cu and COO − , π-π interaction between Taniaphos-Cu and amino acid enantiomers are important acting forces in chiral extraction. The steric-hindrance between NH 2 and OH lead to Taniaphos-Cu-D-Phe is more stable than Taniaphos-Cu-L-Phe. This work provided a chiral extractant that has good abilities to enantioseparate various amino acid enantiomers.

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Determination of Enantiomeric Excess by Solid-Phase Extraction Using a Chiral Metal-Organic Framework as Sorbent

Cited by 8 publications

References 41 publications

Metal–organic frameworks in chiral separation of pharmaceuticals

Metal–organic frameworks in chiral separation of pharmaceuticals

Enantioseparation of amino acid and mandelic acid enantiomers using Garphos derivatives as chiral extractants

Investigation of Taniaphos as a chiral selector in chiral extraction of amino acid enantiomers

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