Isothermal titration calorimetry for chiral chemistry

Werber, Liora; Mastai, Yitzhak

doi:10.1002/chir.22842

Cited by 17 publications

(12 citation statements)

References 71 publications

(104 reference statements)

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“…For further investigation of this hypothesis, isothermal titration calorimetry (ITC) was employed. 57 − 59 This technique offers information on thermodynamic parameters of interactions in the solution and is thus convenient for measuring differences in the interactions between both composites. In the experiments, equal aliquots of one enantiomer of phenylalanine (Phe) were titrated into the dispersion of the l - or d -composite, and the heat response upon injection is monitored.…”

Section: Resultsmentioning

confidence: 99%

“…They are, however, synthesized from two different enantiopure ionic liquids, and it can be expected that they will interact differently with the enantiomers of the same compound if chiral information of the CIL could be transferred to the composites. For further investigation of this hypothesis, isothermal titration calorimetry (ITC) was employed. − This technique offers information on thermodynamic parameters of interactions in the solution and is thus convenient for measuring differences in the interactions between both composites. In the experiments, equal aliquots of one enantiomer of phenylalanine (Phe) were titrated into the dispersion of the l - or d -composite, and the heat response upon injection is monitored.…”

Section: Resultsmentioning

confidence: 99%

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Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation

Perovic

Aloni

Zhang

et al. 2021

ACS Appl. Mater. Interfaces

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Chiral separation and asymmetric synthesis and catalysis are crucial processes for obtaining enantiopure compounds, which are especially important in the pharmaceutical industry. The efficiency of the separation processes is readily increased by using porous materials as the active material can interact with a larger surface area. Silica, metal–organic frameworks, or chiral polymers are versatile porous materials that are established in chiral applications, but their instability under certain conditions in some cases requires the use of more stable porous materials such as carbons. In addition to their stability, porous carbon materials can be tailored for their ability to adsorb and catalytically activate different chemical compounds from the liquid and the gas phase. The difficulties imposed by the functionalization of carbons with chiral species were tackled in the past by carbonizing chiral ionic liquids (CILs) together with a template to create pores, which results in the entire body of a material that is built up from the precursor. To increase the atomic efficiency of ionic liquids for better economic utilization of CILs, the approach presented here is based on the formation of a composite between CIL-derived chiral carbon and a pristine carbon material obtained from carbohydrate precursors. Two novel enantioselective carbon composite materials are applied for the chiral recognition of molecules in the gas phase, as well as in solution. The enantiomeric ratio of the l -composite for phenylalanine from the solution was (L/D) = 8.4, and for 2-butanol from the gas phase, it was (S/R) = 1.3. The d -composite showed an opposite behavior, where the enantiomeric ratio for phenylalanine was (D/L) = 2.7, and for 2-butanol from the gas phase, it was (R/S) = 1.3.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation

Perovic

Aloni

Zhang

et al. 2021

ACS Appl. Mater. Interfaces

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“…Los datos experimentales de la valoración representan potencia frente a tiempo obteniéndose unos picos correspondientes a las adiciones como los representados en la Figura 5B. Mediante la integración de estos picos se obtiene la entalpía asociada a cada inyección, y de la pendiente del ajuste se obtiene la K termodinámica de enlace (Figura 5B) [70].…”

Section: Ii126 Calorimetría De Valoración Isotérmica (Itc)unclassified

“…Figura 5. A) Diagrama representativo de un calorímetro de valoración isotérmica [70]. B) Ejemplo de unos datos obtenidos por ITC y la isoterma derivada de la integración de cada adición [71].…”

Section: Ii126 Calorimetría De Valoración Isotérmica (Itc)unclassified

Interacción de ARN con doxorrubicina: Influencia del ligando y del metal en la actividad biológica de complejos organometálicos

Antolín¹

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“…The chiral discriminatory ability of the those amino acid nanoparticles was demonstrated with the enantioselective crystallization of racemic mixtures of amino acids and by isothermal titration calorimetry (I.T.C) to measure the adsorption energy of enantiomers onto the surface of chiral polymeric nanoparticles. For example, when the conglomerate system of DL asparagine is crystallized in the presence of theses chiral nanoparticles particles, a preferential enantioselective crystallization is observed, with an enantiomeric excess of up to 23 %.…”

Section: Introductionmentioning

confidence: 99%

Chiral Polymers and Polymeric Particles for Enantioselective Crystallization

Medina

Mastai

2018

Israel Journal of Chemistry

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Chiral polymers and chiral polymeric particles have emerged as a new and exciting field of research in recent years mainly due to their possibly applications in chiral chemistry. This paper reviews the present state of the art regarding production techniques for the synthesis and applications of chiral polymeric particles. The main methods for preparing of chiral polymeric particles such as: direct polymerization, emulsion, precipitation, and suspension polymerization of chiral monomers, are reviewed. Moreover, in this article we also present the use of chiral polymers as chiral templates for the synthesis of chiral mesoporous materials. In this review we highlighted the properties and parameters involved in the preparation of these chiral polymeric materials. The present review focuses mainly on the use of chiral polymer and chiral polymeric particles for enantioselective crystallization and enantioseparation. References of the most relevant literature published by various research groups are provided. Anyway, it is clear that chiral polymeric particles are a distinctive type of chiral nanomaterials that can find many new application in other fields like, chiral drug delivery systems, enantioselective catalysis. We hope that this review article will inspired new researchers in this field and will boost the research dealing on chiral polymeric particles especially in their implementation in new areas in chiral chemistry.

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Isothermal titration calorimetry for chiral chemistry

Cited by 17 publications

References 71 publications

Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation

Toward Efficient Synthesis of Porous All-Carbon-Based Nanocomposites for Enantiospecific Separation

Interacción de ARN con doxorrubicina: Influencia del ligando y del metal en la actividad biológica de complejos organometálicos

Chiral Polymers and Polymeric Particles for Enantioselective Crystallization

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