Preparation and characterization of per‐<i>O</i>‐pentylated cyclodextrins

Wenz, Gerhard; Mischnick, Petra; Krebber, Ralph; Richters, Martina; König, Wilfried Α.

doi:10.1002/jhrc.1240131015

Cited by 24 publications

(4 citation statements)

References 20 publications

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“…Hexakis‐(2,3,6‐tri‐O‐pentyl)‐α‐CD 23 (commercially available as, e.g., Lipodex A) 159,160 (cf. Figure 8) is a CD‐based CSP for gas chromatography used for the separation of a broad range of chiral compounds such as carbohydrates, polyols, diols, hydroxy acid esters, (epoxy‐) alcohols, glycerol derivatives, spiroketals, ketones, and alkylhalogenides.…”

Section: Chiral Stationary Phases: Synthesis and Application In Gas C...mentioning

confidence: 99%

Chiral stationary phases and applications in gas chromatography

et al. 2022

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Chiral compounds are ubiquitous in nature and play a pivotal role in biochemical processes, in chiroptical materials and applications, and as chiral drugs. The analysis and determination of the enantiomeric ratio (er) of chiral compounds is of enormous scientific, industrial, and economic importance. Chiral separation techniques and methods have become indispensable tools to separate chiral compounds into their enantiomers on an analytical as well on a preparative level to obtain enantiopure compounds. Chiral gas chromatography and high‐performance liquid chromatography have paved the way and fostered several research areas, that is, asymmetric synthesis and catalysis in organic, medicinal, pharmaceutical, and supramolecular chemistry. The development of highly enantioselective chiral stationary phases was essential. In particular, the elucidation and understanding of the underlying enantioselective supramolecular separation mechanisms led to the design of new chiral stationary phases. This review article focuses on the development of chiral stationary phases for gas chromatography. The fundamental mechanisms of the recognition and separation of enantiomers and the selectors and chiral stationary phases used in chiral gas chromatography are presented. An overview over syntheses and applications of these chiral stationary phases is presented as a practical guidance for enantioselective separation of chiral compound classes and substances by gas chromatography.

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Section: Chiral Stationary Phases: Synthesis and Application In Gas C...mentioning

confidence: 99%

Chiral stationary phases and applications in gas chromatography

et al. 2022

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“…14 What is more, fully alkylated cyclodextrin derivatives, such as per-O-pentylated cyclodextrin, are liquids even below room temperature. 15 However, long-chain substituents in cyclodextrin derivatives are likely to be included within the apolar cavities and reduce the porosity. 1 We intend to prepare the type I porous liquids based on ionic liquid-featured cyclodextrin by taking advantage of ionic liquids, which remain in the liquid phase over a wide range of temperature.…”

Section: Introductionmentioning

confidence: 99%

“…Ogoshi et al developed a new type of liquid cyclodextrin by modification with triethylene oxide . What is more, fully alkylated cyclodextrin derivatives, such as per- O -pentylated cyclodextrin, are liquids even below room temperature . However, long-chain substituents in cyclodextrin derivatives are likely to be included within the apolar cavities and reduce the porosity .…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin Porous Liquid Materials for Efficient Chiral Recognition and Separation of Nucleosides

Wang

Sun

Bian

et al. 2020

ACS Appl. Mater. Interfaces

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Porous liquids are porous materials that have exhibited unique properties in various fields. Herein, we developed a method to synthesize the type I porous liquids via liquefaction of cyclodextrins by chemical modification. The cyclodextrin porous liquids were characterized by Fourier-transform infrared (FTIR) spectroscopy, NMR, matrix-assisted laser desorption ionization-time-of-flight mass spectrometry (MALDI-TOF MS), circular dichroism (CD), and UV−vis spectroscopy. The measured ionic conductivity of the γ-cyclodextrin porous liquid was 500 times as great as that of its reactants, which was found to be the first instance with such great conductivity for a type I porous liquid. What is more, the γ-cyclodextrin porous liquid had been demonstrated experimentally to have outstanding chiral recognition ability toward pyrimidine nucleosides in water, which was further confirmed by computational simulations. Additionally, enantiomeric excess of the extracted nucleoside was achieved up to 84.81% by convenient extraction from the mixture of racemic nucleosides and γcyclodextrin porous liquid. The great features of the novel cyclodextrin porous liquids could bring opportunities in many fields, including the preparation of chiral separation materials, development of new drug screening mechanisms, and construction of chiral response materials.

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“…In this work we describe the preparation of heptakis(6-O-ethyl-2,3-O-pentyl)-b-cyclodextrin, which combines the characteristics of heptakis-(per-O-pentyl)-b-cyclodextrin and heptakis(6-O-methyl-2,3-di-O-pentyl)-b-cyclodextrin derivatives. These compounds show remarkable enantioselective properties [11,12]. Detailed stereochemical investigations may also answer questions related to chemotaxonomy and biosynthetic correlation in plant constituents [13].…”

Section: Introductionmentioning

confidence: 97%