HPLC Enantioseparation on Cyclodextrin-Based Chiral Stationary Phases

Li, Xiaoxuan; Wang, Yong

doi:10.1007/978-1-4939-9438-0_9

Cited by 7 publications

(6 citation statements)

References 37 publications

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“…where the E binding term derived from the contributions of the van der Waals (vdW) and the electrostatic (es) interaction terms (Eq. [ 5]). The term E vdW in turn is composed of repulsive (rep) and dispersive (disp) energy (Eq.…”

Section: Molecular Modeling Of Capillary Electrophoresis Enantioseparations Promoted By Cyclodextrins: Applicationsmentioning

confidence: 99%

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Peluso

Chankvetadze

2021

Electrophoresis

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CDs are cyclic oligosaccharides consisting of α‐d‐glucopyranosyl units linked through 1,4‐linkages, which are obtained from enzymatic degradation of starch. The coexistence of hydrophilic and hydrophobic regions in the same structure makes these macrocycles extremely versatile as complexing host with application in food, cosmetics, environmental, agriculture, textile, pharmaceutical, and chemical industries. Due to their inherent chirality, CDs have been also successfully used as chiral selectors in enantioseparation science, in particular, for CE enantioseparations. In the last decades, multidisciplinary approaches based on CE, NMR spectroscopy, X‐ray crystallography, microcalorimetry, and molecular modeling have shed light on some aspects of recognition mechanisms underlying enantiodiscrimination. With the ever growing improvement of computer facilities, hardware and software, computational techniques have become a useful tool to model at molecular level the dynamics of diastereomeric associate formation to sample low‐energy conformations, the binding energies between the enantiomer and the CD, and to profile noncovalent interactions contributing to the stability of CD/enantiomer association. On this basis, the aim of this review is to provide the reader with a critical overview on the applications of CDs in CE. In particular, the contemporary theory of the electrophoretic technique and the main structural features of CDs are described, with a specific focus on techniques, methods, and approaches to model CE enantioseparations promoted by native and substituted CDs. A systematic compilation of all published literature has not been attempted.

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Section: Molecular Modeling Of Capillary Electrophoresis Enantioseparations Promoted By Cyclodextrins: Applicationsmentioning

confidence: 99%

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Peluso

Chankvetadze

2021

Electrophoresis

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“…The click reaction can realize the construction of bilayer CD-CSP [ 33 ]. Li also reported this bilayer CD-CSP, and achieved complete separation of dansyl- dl -leucine and dansyl- dl -phenylalanine within 30 min [ 34 ].…”

Section: Chromatographic Separationmentioning

confidence: 99%

Chiral Recognition for Chromatography and Membrane-Based Separations: Recent Developments and Future Prospects

et al. 2021

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With the rapid development of global industry and increasingly frequent product circulation, the separation and detection of chiral drugs/pesticides are becoming increasingly important. The chiral nature of substances can result in harm to the human body, and the selective endocrine-disrupting effect of drug enantiomers is caused by differential enantiospecific binding to receptors. This review is devoted to the specific recognition and resolution of chiral molecules by chromatography and membrane-based enantioseparation techniques. Chromatographic enantiomer separations with chiral stationary phase (CSP)-based columns and membrane-based enantiomer filtration are detailed. In addition, the unique properties of these chiral resolution methods have been summarized for practical applications in the chemistry, environment, biology, medicine, and food industries. We further discussed the recognition mechanism in analytical enantioseparations and analyzed recent developments and future prospects of chromatographic and membrane-based enantioseparations.

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“…Many article reviews and book chapters generally describe α-, β-, γ-and modified-cyclodextrins for the separation of enantiomeric compounds by liquid chromatography [76,77]. More recently, Li et al have described the synthesis of a triazole-bridged duplex CD-CSP and its application for the enatioseparation of Dns-Leu and Dns-Phe by HPLC [78]. Shuang et al synthesized a new chiral stationary phase based on β-cyclodextrin for the enantioseparation of five derivatized and three underivatized DL-amino acid enantiomers by high-performance liquid chromatography.…”

Section: Cyclodextrin-based Chiral Stationary Phasesmentioning

confidence: 99%

Recent Advances in Chiral Analysis of Proteins and Peptides

Morvan

Mikšı́k

2021

Separations

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Like many biological compounds, proteins are found primarily in their homochiral form. However, homochirality is not guaranteed throughout life. Determining their chiral proteinogenic sequence is a complex analytical challenge. This is because certain D-amino acids contained in proteins play a role in human health and disease. This is the case, for example, with D-Asp in elastin, β-amyloid and α-crystallin which, respectively, have an action on arteriosclerosis, Alzheimer's disease and cataracts. Sequence-dependent and sequence-independent are the two strategies for detecting the presence and position of D-amino acids in proteins. These methods rely on enzymatic digestion by a site-specific enzyme and acid hydrolysis in a deuterium or tritium environment to limit the natural racemization of amino acids. In this review, chromatographic and electrophoretic techniques, such as LC, SFC, GC and CE, will be recently developed (2018–2020) for the enantioseparation of amino acids and peptides. For future work, the discovery and development of new chiral stationary phases and derivatization reagents could increase the resolution of chiral separations.

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HPLC Enantioseparation on Cyclodextrin-Based Chiral Stationary Phases

Cited by 7 publications

References 37 publications

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Chiral Recognition for Chromatography and Membrane-Based Separations: Recent Developments and Future Prospects

Recent Advances in Chiral Analysis of Proteins and Peptides

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