Enantioselective liquid-liquid extraction of amino acid enantiomers using (S)-MeO-BIPHEP-metal complexes as chiral extractants

Liu, Xiong; Ma, Yu; Cao, Ting; Tan, Danni; Wei, Xinyu; Jin, Can; Yu, Lin

doi:10.1016/j.seppur.2018.09.068

Cited by 29 publications

(30 citation statements)

References 29 publications

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“…After equilibrium is attained, the aqueous phase was filtered by 0.45‐μm filter membrane, and the concentrations of d / l ‐3‐chloro‐phenylglycine were determined by HPLC. The HPLC analysis was carried out using the method described in our precious work . The concentrations of d / l 3‐chloro‐phenylglycine in organic phase were calculated through the subtraction method.…”

Section: Methodsmentioning

confidence: 99%

“…The distribution ratios of l ‐3‐chloro‐phenylglycine ( k l ) and d ‐3‐chloro‐phenylglycine ( k d ) between organic phase and aqueous phase were defined in Equations and , respectively. The operational enantioselectivity ( α ), enantiomeric excess ( ee ), fraction of substrate in organic phase ( f ), and performance factor ( pf ) were defined in Equations , , , and , respectively

k_{L} = \frac{true}{C_{L, org}},

k_{D} = \frac{true}{C_{D, org}},

α = \frac{true}{k_{normalD}} italicor α = \frac{true}{k_{normalL}},

{ee}_{org} = \frac{C_{normalD, org} - C_{normalL, org}}{C_{normalD, org} + C_{normalL, org}},

f = \frac{true}{C_{L, org}},

italicpf = f \times {ee}_{org},

where C l ,w and C d ,w are the concentrations of l ‐ and d ‐3‐chloro‐phenylglycine in water phase at equilibrium, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, some diphosphine ligands used as chiral catalysts in asymmetric reactions have been proved to be effective chiral selectors in enantioselective liquid‐liquid extraction (ELLE) . For instance, ( S )‐BINAP‐metal, ( S )‐MeO‐BIPHEP‐metal, and ( S )‐SEGPHOS‐metal complexes have considerable abilities to separate amino acid and mandelic acid enantiomers . Since the chiral ligands in asymmetric reactions may be the good chiral selectors, it seemed interesting to further study this field with the goal of finding more ligands with favorable enantiomeric recognition and separation potency in ELLE.…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective liquid‐liquid extraction of 3‐chloro‐phenylglycine enantiomers using (S,S)‐DIOP as extractant

Xiong

et al. 2019

Chirality

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(S,S)‐DIOP, a common catalyst used in asymmetric reaction, was adopted as chiral extractant to separate 3‐chloro‐phenylglycine enantiomers in liquid‐liquid extraction. The factors affecting extraction efficiency were studied, including metal precursors, organic solvents, extraction temperature, chiral extractant concentration, and pH of aqueous phase. (S,S)‐DIOP‐Pd exhibited good ability to recognize 3‐chloro‐phenylglycine enantiomers, and the operational enantioselectivity (α) is 1.836. The highest performance factor (pf) was obtained under the condition of extraction temperature of 9.1°C, (S,S)‐DIOP‐Pd concentration of 1.7 mmol/L, and pH of aqueous phase of 7.0. In addition, the possible recognition mechanism of (S,S)‐DIOP‐Pd towards 3‐chloro‐phenylglycine enantiomers was discussed.

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Section: Methodsmentioning

confidence: 99%

k_{L} = \frac{true}{C_{L, org}},

k_{D} = \frac{true}{C_{D, org}},

α = \frac{true}{k_{normalD}} italicor α = \frac{true}{k_{normalL}},

{ee}_{org} = \frac{C_{normalD, org} - C_{normalL, org}}{C_{normalD, org} + C_{normalL, org}},

f = \frac{true}{C_{L, org}},

italicpf = f \times {ee}_{org},

where C l ,w and C d ,w are the concentrations of l ‐ and d ‐3‐chloro‐phenylglycine in water phase at equilibrium, respectively.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Enantioselective liquid‐liquid extraction of 3‐chloro‐phenylglycine enantiomers using (S,S)‐DIOP as extractant

Xiong

et al. 2019

Chirality

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“…Among these chiral extractants, metal complex has attracted more and more attention just because of its high enantioselectivity and efficiency. 23 These results indicated that chiral diphosphine ligands are excellent chiral extractants in enantioselective liquid-liquid extraction. [8][9][10][11][12][13][14][15] The chemical structures of these chiral diphosphine ligands are shown in Figure 1.…”

Section: Introductionmentioning

confidence: 90%

“…23 The extraction process is as follows: 2.0 mL of chiral extractants solution and 2.0 mL of mandelic acid enantiomers solution were added in a test tube. 23 The extraction process is as follows: 2.0 mL of chiral extractants solution and 2.0 mL of mandelic acid enantiomers solution were added in a test tube.…”

Section: Enantioselective Liquid-liquid Extraction Of Dl-mandelic Acidmentioning

confidence: 99%

Enantioselective liquid‐liquid extraction of DL‐mandelic acid using chiral diphosphine ligands as extractants

Liu

Zhou

et al. 2019

Chirality

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In order to expand the application range of chiral diphosphine ligands, (S)-BINAP, (S)-SEGPHOS, and (S)-MeO-BIPHEP were employed as extractants to recognize DL-mandelic acid. The results indicated that (S)-SEGPHOS-Cu exhibited considerable ability to recognize DL-mandelic acid with operational enantioselectivity (α) of 2.677. The process of extraction of DL-mandelic acid using (S)-SEGPHOS-Cu as extractant was systematically investigated. Performance factor (pf) was adopted to comprehensively evaluate the extraction. After optimization by response surface methodology (RSM), the optimal extraction condition is temperature of 5.5°C, (S)-SEGPHOS-Cu concentration of 3.0 mmol/L, and pH of 8.0. And the predicted and experimental maximum values of pf were 0.26374 and 0.26839, respectively. KEYWORDS (S)-BINAP, (S)-MeO-BIPHEP, (S)-SEGPHOS, enantioselective liquid-liquid extraction, mandelic acid

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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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Enantioselective liquid-liquid extraction of amino acid enantiomers using (S)-MeO-BIPHEP-metal complexes as chiral extractants

Cited by 29 publications

References 29 publications

Enantioselective liquid‐liquid extraction of 3‐chloro‐phenylglycine enantiomers using (S,S)‐DIOP as extractant

Enantioselective liquid‐liquid extraction of 3‐chloro‐phenylglycine enantiomers using (S,S)‐DIOP as extractant

Enantioselective liquid‐liquid extraction of DL‐mandelic acid using chiral diphosphine ligands as extractants

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

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