Eutectic solvents formed by (+)-DTTA and L-menthol as novel chiral recognition and separation media for enantioselective extraction of valsartan enantiomers

Chen, Lin; Ge, Li; Liang, Qinghui; Zhao, Zhigang; Yang, Kang

doi:10.1016/j.molliq.2022.120818

Cited by 3 publications

(5 citation statements)

References 37 publications

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“…As illustrated in Figure 10A, both the distribution coefficients K L and K D increase with the temperature increasing, which is owing to the accelerated mass transfer of enantiomers at high extraction temperature. As a result, the enantioselectivity and enantiomeric excess values (see Figure 10B) first increase and then decrease at the temperature of 25°C, indicating that excessive temperature would weaken the complexation interaction of chiral selector with ofloxacin enantiomer and therefore reduce the separation performance of the BRCE system 41,42 . In a word, the BRCE system can be carried out at room temperature without additional heating.…”

Section: Resultsmentioning

confidence: 99%

“…As a result, the enantioselectivity and enantiomeric excess values (see Figure 10B) first increase and then decrease at the temperature of 25 C, indicating that excessive temperature would weaken the complexation interaction of chiral selector with ofloxacin enantiomer and therefore reduce the separation performance of the BRCE system. 41,42 In a word, the BRCE system can be carried out at room temperature without additional heating.…”

Section: Effect Of Extraction Temperature On Brce Performancementioning

confidence: 99%

“…For example, Ding et al 41 used the DFT method to study the chiral recognition mechanism for a series of CILs with amlodipine enantiomers and discovered a correlation between interaction energy difference and enantioselectivity. Similarly, Chen et al 42 revealed that the eutectic solvent formed by L-menthol and (+)-di-p-toluoyl-D-tartaric acid (D-DTTA) has chiral recognition ability for the resolution of valsartan racemate through the analysis of interaction energy using DFT method. Zhao et al 43 As a chiral drug, L-ofloxacin exhibits more potent antimicrobial activity and a broader antibacterial spectrum than D-ofloxacin and ofloxacin racemate, while also demonstrating lower toxic side effects.…”

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confidence: 99%

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Enhancement of separation performance for ofloxacin enantiomers by a biphasic recognition chiral extraction system

Li,

Cheng,

2024

AIChE Journal

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Despite greatly improved separation performance towards many mixtures, utilizing biphasic recognition chiral extraction (BRCE) systems in enantiomer separation remains challenging due to inadequate comprehension of chiral recognition and biphasic synergism mechanisms. In this work, using ofloxacin enantiomers as a case study, separation performance of BRCE system is systematically examined from experimental and theoretical aspects. The BRCE system, comprising di‐p‐toluoyl‐l‐tartaric acid and β‐cyclodextrin as hydrophobic and hydrophilic selectors, achieves maximum enantioselectivity and enantiomeric excess values of 2.4 and 26% under optimal conditions. Five‐stage counter‐current extraction and reverse extraction significantly improve the enantiomeric excess value up to 91%. Molecular simulations reveal that to construct an enhanced BRCE system, two chiral selectors should have opposite recognition abilities for target enantiomers and weak interactions between themselves. This work provides guidance on selecting suitable selectors for construction of an enhanced BRCE system not only for separating ofloxacin enantiomers but also other enantiomers.

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Section: Resultsmentioning

confidence: 99%

Section: Effect Of Extraction Temperature On Brce Performancementioning

confidence: 99%

mentioning

confidence: 99%

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Enhancement of separation performance for ofloxacin enantiomers by a biphasic recognition chiral extraction system

Li,

Cheng,

2024

AIChE Journal

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“…To separate chiral molecules, several methods have been investigated, including crystallization, biological, and chromatographic methods. – Thereinto, chemical reagent separation has become the main method because of the simplicity, high-speed, and general application . In the mechanism, chemical reagents (acid or base) interact with the chiral pharmaceutical (base or acid) to form a mixture of diastereoisomers, which can then be separated by suitable methods such as crystallization .…”

Section: Introductionmentioning

confidence: 99%

“…12−15 Thereinto, chemical reagent separation has become the main method because of the simplicity, high-speed, and general application. 16 In the mechanism, chemical reagents (acid or base) interact with the chiral pharmaceutical (base or acid) to form a mixture of diastereoisomers, which can then be separated by suitable methods such as crystallization. 17 Nevertheless, soluble reagents make the purification of chiral drugs low-efficiency and weak-recyclability, especially the production of chiral drugs is increasing dramatically every year.…”

Section: Introductionmentioning

confidence: 99%

Synergetic Patterns of Chiral Fragments and Steric Confinement for the Separation of Chiral Pharmaceuticals

Geng,

Cui,

et al. 2023

J. Phys. Chem. C

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Chiral drug molecules play an important role in the treatment of diseases and public health; however, these substances are often difficult to be separated from nonchiral molecules in the chemical production process. Here, a chiral molecule, 3,5-dibromo-Ltyrosine, is adopted as the building monomer to cross-link with 1,3,5tris(4-ethynylphenyl)benzene through the Sonogashira−Hagihara coupling reaction to obtain the chiral PAF solid, LNU-56. Because we have successfully introduced chiral amino acid groups into the pores with a diameter of 1.2 nm, the obtained adsorbent shows outstanding adsorption capability for ketoprofen drug, with a maximum capacity of 725.56 mg g −1 , which is the highest adsorption capacity reported so far. Meanwhile, synergetic patterns of chiral fragments and steric confinement bring about the high selectivity for chiral pharmaceuticals in the presence of various achiral drugs, various interfering ions, or high concentration of NaCl. The advantages of constructing a chiral porous platform provide new perspectives on the development of PAF-based adsorbents and separation and purification of pharmaceuticals.

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Chiral drugs: Sources, absolute configuration identification, pharmacological applications, and future research trends

Peng,

Zhu,

Luo

et al. 2024

LabMed Discovery

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Eutectic solvents formed by (+)-DTTA and L-menthol as novel chiral recognition and separation media for enantioselective extraction of valsartan enantiomers

Cited by 3 publications

References 37 publications

Enhancement of separation performance for ofloxacin enantiomers by a biphasic recognition chiral extraction system

Enhancement of separation performance for ofloxacin enantiomers by a biphasic recognition chiral extraction system

Synergetic Patterns of Chiral Fragments and Steric Confinement for the Separation of Chiral Pharmaceuticals

Chiral drugs: Sources, absolute configuration identification, pharmacological applications, and future research trends

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