Enantioseparation of 3-Chlorophenylglycine enantiomers using Mandyphos-Pd as chiral extractant

Liu, Xiong; Chen, Shuhuan; Ma, Yu; Xiao, Wenjie

doi:10.1016/j.cjche.2020.08.009

Cited by 6 publications

(10 citation statements)

References 33 publications

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“…Generally, there was a small amount of racemic amino acid in organic phase that was extracted by physical dissolution with non-stereoselectivity. 29 This phenomenon would decrease the ee values when Taniaphos-Cu concentration was low. Thus, the curves of ee in Figure 3 were positively correlated with Taniaphos-Cu concentration in the range of 0.25-1.0 mmol/L.…”

Section: Enantioselectivities Of Taniaphos-cu At Different Concentrationmentioning

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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Section: Enantioselectivities Of Taniaphos-cu At Different Concentrationmentioning

confidence: 99%

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

et al. 2021

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“…Our previous works have indicated that some diphosphonic catalysts are good chiral extractants. The recognition mechanism analysis revealed that the coordination between extractant and −COO − /−NH 2 , π–π interaction between aryl groups and steric effect are the main acting forces in chiral recognition 22,23 . The mechanism analysis provided an important theoretical guidance for discovering new and efficient chiral extractants.…”

Section: Introductionmentioning

confidence: 95%

“…The recognition mechanism analysis revealed that the coordination between extractant and ÀCOO À /ÀNH 2 , π-π interaction between aryl groups and steric effect are the main acting forces in chiral recognition. 22,23 The mechanism analysis provided an important theoretical guidance for discovering new and efficient chiral extractants. Josiphos((R)-1-[(S)-2-(Diphenylphosphino)ferrocenyl]ethyldi (3,5-xylyl) phosphine) is a ferrocene diphosphonic ligand, which has been proved to be an efficient catalyst for asymmetric transfer hydrogenation.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of amino acid and mandelic acid enantiomers using Josiphos‐metal complexes as chiral extractants

Wang

Yang²,

Qin

et al. 2023

Chirality

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The development of new and efficient chiral extractants has always been the research hotspot and difficulty in the field of chiral extraction. Josiphos, a famous ferrocene derivative catalyst, is employed as a chiral extractant in enantioseparation of amino acid and mandelic acid enantiomers. The influences of metal ions, organic solvents, pH of the aqueous solution, extractant concentrations, and extraction temperature on enantioselectivities are systematically studied. The result reveals that Josiphos-Pd has good capabilities to enantioseparate 4-nitro-phenylalanine (Nphe), 3-chloro-phenylglycine (Cpheg), and mandelic acid (MA) with separation factors (α) of 3.30, 2.65, and 2.18, respectively. The pH of the aqueous phase and Josiphos-Pd concentration affect the extraction significantly, whereas extraction temperature shows little influence. After optimizing by response surface method, the mathematical models for extractions are established. And the highest experimental performance factors (pf ) for Nphe, Cpheg, and MA are 0.1843, 0.1335, and 0.08884, respectively.

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“…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 . Chiral extraction is a promising method to separate optically pure enantiomer which has the advantages of simple process, low cost, and high recovery 4,10,11 .…”

Section: Introductionmentioning

confidence: 99%

“…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. 4,10,11 Chiral extractant plays a key role in the enantioseparation of enantiomers.…”

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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Enantioseparation of 3-Chlorophenylglycine enantiomers using Mandyphos-Pd as chiral extractant

Cited by 6 publications

References 33 publications

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

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

Enantioseparation of amino acid and mandelic acid enantiomers using Josiphos‐metal complexes as chiral extractants

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

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