Enantioseparation of 4-Nitrophenylalanine using (S)-SDP-metal complex as chiral extractant

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

doi:10.1016/j.seppur.2020.116547

Cited by 13 publications

(11 citation statements)

References 33 publications

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“…This phenomenon was similar to other diphosphine ligands reported in previous studies. 13,17 However, k D and k L for other amino acid enantiomers were both decreased with increasing temperature. And the values of α remained stable with increasing temperature.…”

Section: Enantioselectivities Of Taniaphos-cu At Different Temperaturementioning

confidence: 96%

“…The precious works suggested that Chlorobenzene would disturb the π-π interaction of phenyl groups between chiral extractants and substrates. [15][16][17] Accordingly, π-π interaction between Taniaphos-Cu and amino acid enantiomers might be an important acting force in chiral extraction.…”

Section: Extraction Of Amino Acid Enantiomers Using Different Organic Solventsmentioning

confidence: 99%

“…16 (S)-SDP is a spiro ligand that could be used as chiral selector in chiral extraction of 4-Nitrophenylalanine with α of 3.32. 17 However, all these non-biphenyl (binaphthalene) diphosphine ligands only showed separation ability to one kind of amino acid enantiomers. Finding chiral selector with high stereoselectivity to a variety of amino acid enantiomers remains a challenge and warrants further research.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Enantioselectivities Of Taniaphos-cu At Different Temperaturementioning

confidence: 96%

Section: Extraction Of Amino Acid Enantiomers Using Different Organic Solventsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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“…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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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 4-Nitrophenylalanine using (S)-SDP-metal complex as chiral extractant

Cited by 13 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

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

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

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