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

期刊

ELECTROPHORESIS
卷 42, 期 17-18, 页码 1676-1708

出版社

WILEY
DOI: 10.1002/elps.202100053

关键词

Capillary electrophoresis; Computational methods; Cyclodextrins; Enantioseparation; Molecular modeling

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Cyclodextrins (CDs) are versatile cyclic oligosaccharides obtained from starch degradation, with applications in various industries due to their hydrophilic and hydrophobic regions. Their inherent chirality allows for successful use as chiral selectors, while multidisciplinary approaches have shed light on recognition mechanisms. Computational techniques have become useful in modeling molecular dynamics, binding energies, and noncovalent interactions between CD and enantiomers.
CDs are cyclic oligosaccharides consisting of alpha-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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