Enantioselective liquid-liquid extraction of tryptophan enantiomers by a recyclable aqueous biphasic system based on stimuli-responsive polymers

Ma, Shaoping; Li, Fenfang; Tan, Zhijian

doi:10.1016/j.chroma.2021.462532

Cited by 9 publications

(9 citation statements)

References 49 publications

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“…In extraction system, there are one or two phases that have chiral environments, leading to enantiomers having different distribution coefficients. So, finding new chiral extractants with high stereoselectivity and efficiency has always been the research hotspot and difficulty in the field of chiral extraction 19–21 . Our previous works have indicated that some diphosphonic catalysts are good chiral extractants.…”

Section: Introductionmentioning

confidence: 99%

“…So, finding new chiral extractants with high stereoselectivity and efficiency has always been the research hotspot and difficulty in the field of chiral extraction. [19][20][21] Our previous works have indicated that some diphosphonic catalysts are good chiral extractants. 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.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Introductionmentioning

confidence: 99%

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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“…Double-stimuli-responsive systems provide a higher degree of customization of the target application and thus can be more easily adapted to industrial applications. Combining a thermo-sensitive polymer and a pH-sensitive polymer as the phase-forming agents is the most pursued route to develop double-stimuli-responsive ABS. − To the best of our knowledge, the development of IL-based ABS with double responsiveness to temperature and pH was not previously reported.…”

Section: Introductionmentioning

confidence: 99%

Double-Stimuli-Responsive (Temperature and pH) Aqueous Biphasic Systems Comprising Ionic Liquids

Rufino

Bola

Capela

et al. 2023

ACS Sustainable Chem. Eng.

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Aqueous biphasic systems (ABS) can integrate multiple unit operations and operate under continuous mode, contributing to the development of sustainable separation processes. Encouraged by the designer solvent features of ionic liquids (ILs), we herein propose their use as components of double-stimuli-responsive (temperature- and pH-driven) ABS. Resorting to choline-alkanoate-based ILs as the pH-responsive components and poly(propylene glycol) (PPG 400) as the thermo-responsive component, the ABS ternary phase diagrams are determined at various temperature (25–45 °C) and pH (3–7) conditions. While the liquid–liquid phase diagram response to temperature obeys a lower critical solution temperature-like behavior, the response to pH correlates with the pK a of the IL anion parent acid. The simultaneous responsiveness to temperature and pH is then shown, whose results inspire the development of customizable separation techniques as proved with the simultaneous (one-step) separation of two dyes. By a proper customization of the IL chemical structure and stimuli applied, ABS may be designed to improve the performance and sustainability of separation processes.

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“…Enantioselective liquid–liquid extraction (ELLE) is a promising method for the preparation of optically pure compounds in the points that its easy scale‐up, one liquid layer can be permanently reused, and automatic flow processes might be accessible 14–20 . Though a good deal of chiral extractors (CEs) for ELLE has been developed in last decades for enantioselective extraction of amino acids, they experience low enantioselectivities and often do not work for underivatized forms 21–27 . Binaphthol‐based chiral aldehydes and ketones represented by 1 in Figure 1, on the other hand, have been reported to act as chirality conversion reagents (CCRs) 28,29 or CEs 30–32 for underivatized amino acids through reversible imine bond formation, with relatively high enantioselectivities.…”

Section: Introductionmentioning

confidence: 99%

“…[14][15][16][17][18][19][20] Though a good deal of chiral extractors (CEs) for ELLE has been developed in last decades for enantioselective extraction of amino acids, they experience low enantioselectivities and often do not work for underivatized forms. [21][22][23][24][25][26][27] Binaphthol-based chiral aldehydes and ketones represented by 1 in Figure 1, on the other hand, have been reported to act as chirality conversion reagents (CCRs) 28,29 or CEs [30][31][32] for underivatized amino acids through reversible imine bond formation, with relatively high enantioselectivities.…”

Section: Introductionmentioning

confidence: 99%

Remarkable enantioselectivity enhancement of the extractors with nonaxial chirality in liquid–liquid extraction of underivatized amino acids by introducing t‐butyl group

et al. 2022

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A class of carbonyl extractors, (R)‐3, (R)‐4, and (R)‐5, with nonaxial chirality containing asymmetric carbons has been synthesized and studied for their efficiencies in enantioselective liquid–liquid extraction for underivatized amino acids. The bulky t‐butyl ketone extractors, (R)‐4 and (R)‐5, showed the stereoselectivities ranging 5.4–9.4 of l/d ratio much better than those of the aldehyde extractor, (R)‐3, ranging 2.4–5.2. The imine formation rates and yields of the t‐butyl ketones were not significantly affected by their bulkiness and even in the absence of resonance‐assisted hydrogen bond. This work confirms that a bulky t‐butyl ketone can be a good choice in the development of an extractor not only with axial chirality but also with nonaxial chirality for the enantioselective extraction of unprotected amino acids.

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Enantioselective liquid-liquid extraction of tryptophan enantiomers by a recyclable aqueous biphasic system based on stimuli-responsive polymers

Cited by 9 publications

References 49 publications

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

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

Double-Stimuli-Responsive (Temperature and pH) Aqueous Biphasic Systems Comprising Ionic Liquids

Remarkable enantioselectivity enhancement of the extractors with nonaxial chirality in liquid–liquid extraction of underivatized amino acids by introducing t‐butyl group

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