Regularities between Separations of Enantiomeric and Diastereoisomeric Mixtures. Prediction of the Efficiency of Diastereomeric/ Enantiomeric Separations on the Basis of Behaviour of Enantiomeric Mixtures

Pálovics, Emese; Szeleczky, Zsolt; Bagi, Péter; Faigl, Ferenc; Fogassy, Elemér

doi:10.3311/ppch.7328

Cited by 6 publications

(7 citation statements)

References 25 publications

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“…Considering the acidic resolving agents, L ‐(+)‐tartaric acid and its derivatives were always a popular choice to separate the enantiomers of chiral basic compounds . According to Kozma et al, the 34% of the resolution examples for racemic bases were elaborated using L ‐(+)‐tartaric acid.…”

Section: Resultsmentioning

confidence: 99%

“…the enantiomers of chiral basic compounds. 31,32 According to Kozma et al, 30 the 34% of the resolution examples for racemic bases were elaborated using L-(+)-tartaric acid. The L-(+)tartaric acid has a eutectic composition (ee EUres ) of 95%, which shows good parity with the average enantiomeric purity ( = 98%) of the enantiomeric mixtures of chiral basic compounds separated with this resolving agent (Table 3).…”

Section: Role Of Eutectic Compositionmentioning

confidence: 99%

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Selecting Resolving Agents with Respect to Their Eutectic Compositions

et al. 2016

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In order to develop a resolution procedure for a given racemic compound, the first and the most important step is finding the most suitable resolving agent. We studied 18 individual resolutions that were carried out with resolving agents having high eutectic composition. We found that very high enantiomeric excess values were obtained in all cases. We assume that the eutectic composition of a given resolving agent is one of the most important properties that should always be considered during the search for the most efficient resolving agent.

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Section: Resultsmentioning

confidence: 99%

Section: Role Of Eutectic Compositionmentioning

confidence: 99%

Selecting Resolving Agents with Respect to Their Eutectic Compositions

et al. 2016

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“…The saturation range has not been investigated here but may be also important since many MIPs are imprinted with chiral templates (propranolol is one of them), and thus the adsorption of racemic mixtures on chiral MIPs may prove to be useful in preparative chiral separations [42].…”

Section: Generalization Of the Methodsmentioning

confidence: 99%

Relationship between Individual and Competitive Adsorption Isotherms on Molecularly Imprinted Polymers

Dorkó

Tamás

Horvai

2016

Period. Polytech. Chem. Eng.

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Molecularly imprinted polymers (MIP) are a new generation of selective adsorbents. In practical applications of MIPs Keywords molecularly imprinted polymer, adsorption isotherm, competitive adsorption isotherm, propranolol, beta blocker IntroductionMolecularly imprinted polymers (MIP) are a new generation of selective adsorbents. They are the subject of vigorous research which produces hundreds of papers annually. After years of fundamental research the time appears to be ripe now for their practical applications. This is attested by the increasing number of patent applications (62 in MIPs are typically made by polymerization of suitable monomers in the presence of a so-called template compound. After polymerization the template is removed from the polymer. This procedure leaves empty binding sites in the polymer, which are chemical and geometrical imprints of the template molecule. Due to these sites the MIP can rebind from solutions the template or other molecules which are chemically related to the template. The rebinding on a good MIP occurs selectively against compounds which are not very closely related to the template. The target compound of a practical application can be either the template or a closely related compound (e.g. if the template is expensive or toxic or its bleeding would disturb). Eventually a group of closely related compounds to the template may be targeted.For successful practical applications one needs to know if the MIP will show sufficient selectivity. Quantification of selectivity is a difficult problem in chemistry, and particularly in analytical chemistry [20][21][22][23][24][25]. In the case of MIPs one may rely on a large body of experience in relation to chromatographic adsorbents. The selectivity of liquid chromatographic stationary phases is easily characterized (in a given eluent) if the adsorption isotherms of all adsorbed solutes are linear. In this case selectivity between two adsorbable compounds can be given by the ratio of the respective isotherm slopes, i.e., by the ratio of the respective,

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“…Asymmetric techniques, such as aldol reaction [13], epoxide opening [14], ketone reduction [15] or kinetic resolution of racemic mixtures [16] are well known methods to produce pure enantiomers of alcohols. On the other hand, synthesis of enantiopure amines can rely on asymmetric synthesis catalyzed by chiral metal-ligand complexes [17], differential crystallization of their diastereomeric salts with chiral ligands [18,19] and diverse resolution methods [20]. It is important to note that most of asymmetric chemical catalysts have their biopair in form of enzymes and applied as biocatalyst such as oxidoreductases [21,22], transferases [23], hydrolases [24] or lyases [25].…”

Section: Introductionmentioning

confidence: 99%

Lipase B from Candida antarctica Immobilized on Epoxy-functionalized Hollow Silica Microspheres: Efficient Biocatalysts for Enantiomer Selective Acylation of Alcohols and Amines

Olah

Suba

Boros³

et al. 2018

Period. Polytech. Chem. Eng.

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Hollow silica microspheres with promising physical properties (MAT540TM) as support for enzyme immobilization and biocatalyst were investigated in this study. The amine-functionalized MAT540TM was activated by six bisepoxides inclosing different spacers and used as epoxy-functionalized carrier for immobilization of lipase B from Candida antarctica (CaLB). The novel, covalently fixed CaLB biocatalysts were compared in kinetic resolution (KR) of racemic 1-phenyethanol rac-1 and five racemic amines rac-3a-e using shaken flasks and continuous-flow packed-bed microreactors. Mechanic stability, re-usability and the effect of temperature (0–90 °C) on productivity and enantiomer selectivity of the covalently immobilized CaLB were investigated. The best performing CaLB biocatalyst showed good mechanic stability after 24 h operation time in continuous-flow mode at 60 °C and provided in KRs of racemic 1-phenyethanol rac-1 with vinyl acetate and of five racemic amines with isopropyl 2-ethoxyacetate as acylating agent the non-reacted (S)-alcohol [(S)-1] or (S)-amines [(S)-3a-e] and the forming (R)-ester [(R)-2] or (R)-amide [(R)-4a-e] in good yields with high enantiomeric excess (ee > 99 %, for all).

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Regularities between Separations of Enantiomeric and Diastereoisomeric Mixtures. Prediction of the Efficiency of Diastereomeric/ Enantiomeric Separations on the Basis of Behaviour of Enantiomeric Mixtures

Abstract: Abstract

Cited by 6 publications

References 25 publications

Selecting Resolving Agents with Respect to Their Eutectic Compositions

Selecting Resolving Agents with Respect to Their Eutectic Compositions

Relationship between Individual and Competitive Adsorption Isotherms on Molecularly Imprinted Polymers

Lipase B from Candida antarctica Immobilized on Epoxy-functionalized Hollow Silica Microspheres: Efficient Biocatalysts for Enantiomer Selective Acylation of Alcohols and Amines

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