Enantioseparation of mandelic acid on vancomycin column: Experimental and docking study

Shahnani, Mostafa; Sefidbakht, Yahya; Maghari, Shokoofeh; Mehdi, Ahmad; Rezadoost, Hassan; Ghassempour, Alireza

doi:10.1002/chir.23273

Cited by 15 publications

(14 citation statements)

References 39 publications

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“…Table 1 demonstrates the elemental analysis of epoxy‐ and azide‐functionalized silica as well as ND‐CSP. Based on the results, a major rise was observed in the elemental amounts of N, C, and H. The surface coverage degree for ND‐CSP was calculated by the subsequent equation 42,43 :

\begin{matrix} lefttrue \\ ND - CSP (μmol {normalm}^{- 2}) \\ = \frac{% X \times 10^{6}}{M_{X} \times N_{X} \times S_{A} \times (100 - % C - % H - % N)} \\ = 1.399 \end{matrix}

…”

Section: Resultsmentioning

confidence: 99%

“…The immobilization of the noscapine derivative on azide‐functionalized silica provided 1.399 μmol m −2 selector loading. This amount is more considerable compared to 0.51 and 0.93 μmol m −2 of β‐cyclodextrin, 1.22 μmol m −2 of Whelk‐O1, and 0.46 μmol m −2 vancomycin chiral stationary phase 43–46 . The column capacity for enantioresolution is highly influenced by the bonding density of CSP; thus, the high chiral selector loading for the noscapine derivative will enhance the chromatographic performance.…”

Section: Resultsmentioning

confidence: 99%

“…Figure 3 displays the chromatogram of propranolol enantiomers with R s = 2.26, which is higher than the hydroxypropyl-γ-cyclodextrin monolithic CSP with R s = 0.53, 53 teicoplanin monolith CSP with R s = 1.74, 54 and vancomycin column with R s = 2.0. 43 In comparison with common chiral stationary phases, the resolution of propranolol enantiomers on ND-CSP is higher than amylose tris (3-chloro-5-methylphenylcarbamate) 55 and the amylose tris (3,5-dichlorophenylcarbamate). 56 It seems that the propranolol's second enantiomer had more stable interaction with the noscapine derivative and spread through the column; consequently, band broadening has happened.…”

Section: Hplc Enantioseparationmentioning

confidence: 97%

“…Figure 4 illustrates the chromatogram of mandelic acid enantiomers with R s = 2.73, in which stereoisomers were resolved more suitable and quickly as compared to the vancomycin chiral column with R s = 1.94. 43 The R,S-mandelic acid is a molecule that cannot be easily resolved even with some commercial chiral stationary phases, for instance, the CHIRALPAK ® ZWIX (+). 57 Enantiomeric resolution of a sulfanilamide derivative occurred by using a mobile phase composed of methanol/water (80/20 v/v%), 0.2% TEA.…”

Section: Hplc Enantioseparationmentioning

confidence: 99%

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A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

et al. 2022

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Noscapine is an isolated compound from the opium poppy, with distinctive chiral structure and chemistry, interacts with other compounds due to having multiple π‐acceptors, hydrogen bond acceptors, and ionic sites. Therefore, it has promising applicability for the enantioselective separation of a wide range of polar, acidic, basic, and neutral compounds. A new noscapine derivative chiral stationary phase (ND‐CSP) has been synthesized by consecutive N‐demethylation, reduction, and N‐propargylation of noscapine followed by attachment of a solid epoxy‐functionalized silica bed through the 1,3‐dipolar Huisgen cycloaddition. The noscapine derivative‐based stationary phase provides a considerable surface coverage, which is greater than some commercial CSPs and can validate better enantioresolution performance. The major advantages inherent to this chiral selector are stability, reproducibility after more than 200 tests, and substantial loading capacity. The characterization by Fourier transform infrared (FTIR) spectroscopy and elemental analysis indicated successful functionalization of the silica surface. Chromatographic method conditions like flow rate and mobile phase composition for enantioseparation of various compounds such as warfarin, propranolol, mandelic acid, and a sulfanilamide derivative were optimized. Comparing the experimental results with docking data revealed a clear correlation between the calculated binding energy of ND‐CSP and each enantiomer with the resolution of enantiomer peaks.

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\begin{matrix} lefttrue \\ ND - CSP (μmol {normalm}^{- 2}) \\ = \frac{% X \times 10^{6}}{M_{X} \times N_{X} \times S_{A} \times (100 - % C - % H - % N)} \\ = 1.399 \end{matrix}

…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Hplc Enantioseparationmentioning

confidence: 97%

Section: Hplc Enantioseparationmentioning

confidence: 99%

See 2 more Smart Citations

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

et al. 2022

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“…The new sorbent showed good efficiencies and reduced analysis times in the separation of β-blocker enantiomers. Vancomycin was bonded to silica gel through a carboxylic acid linker made with succinic anhydride [ 33 ]. The functionalization of the silica surface was characterized, and the newly synthesized CSP was successfully applied for the separation of mandelic acid enantiomers in NP mode using n -heptane/2-propanol/TFA.…”

Section: Recent Applications Of Different Macrocyclic Antibiotic-based Cspsmentioning

confidence: 99%

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

et al. 2021

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Numerous chemical compounds of high practical importance, such as drugs, fertilizers, and food additives are being commercialized as racemic mixtures, although in most cases only one of the isomers possesses the desirable properties. As our understanding of the biological actions of chiral compounds has improved, the investigation of the pharmacological and toxicological properties has become more and more important. Chirality has become a major issue in the pharmaceutical industry; therefore, there is a continuous demand to extend the available analytical methods for enantiomeric separations and enhance their efficiency. Direct liquid chromatography methods based on the application of chiral stationary phases have become a very sophisticated field of enantiomeric separations by now. Hundreds of chiral stationary phases have been commercialized so far. Among these, macrocyclic glycopeptide-based chiral selectors have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance. This review focuses on direct liquid chromatography-based enantiomer separations, applying macrocyclic glycopeptide-based chiral selectors. Special attention is paid to the characterization of the physico-chemical properties of these macrocyclic glycopeptide antibiotics providing detailed information on their applications published recently.

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Novel ethylenediamine‐β‐cyclodextrin grafted membranes for the chiral separation of mandelic acid and its derivatives

Zhou,

Wei,

et al. 2024

Chirality

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In the present study, flat cellulose acetate ultrafiltration membranes were prepared first by nonsolvent induced phase separation method. Then chiral membranes for separating the enantiomers were prepared by grafting the ultrafiltration membranes using ethylenediamine‐β‐cyclodextrin as the chiral selector and epichlorohydrin as the spacer arm. The pure water permeability of the ultrafiltration membrane was around 115 L·m−2·h−1·bar−1. The properties of the chiral membranes were characterized using infrared spectroscopy (ATR‐FTIR), X‐ray photoelectron spectroscopy (XPS), and scanning electron microscopy (SEM). The chiral membrane performance in enantiomer separation was evaluated with racemates, such as mandelic acid (MA), 2‐chloromandelic acid (2‐ClMA), 4‐chloromandelic acid (4‐ClMA), and methyl mandelate (MM). The influence of feed concentration on the separation efficiency was also investigated. The results indicated that the enantiomeric excess percentages (e.e%) of the racemic mixtures for these four chiral compounds were up to 31.8%, 25.4%, 17.8%, and 32.6%, respectively. The binding free energy of the chiral selector with the (S)‐enantiomer calculated by molecular dynamics simulations was stronger than that with the (R)‐enantiomer, which was consistent with the experimental results (higher concentration of (R)‐enantiomer in the permeate). This supports the affinity absorption‐separation mechanism.

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Enantioseparation of mandelic acid on vancomycin column: Experimental and docking study

Cited by 15 publications

References 39 publications

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

A new chiral stationary phase based on noscapine: Synthesis, enantioseparation, and docking study

Enantioselective Liquid Chromatographic Separations Using Macrocyclic Glycopeptide-Based Chiral Selectors

Novel ethylenediamine‐β‐cyclodextrin grafted membranes for the chiral separation of mandelic acid and its derivatives

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