Cyclodextrins

Scriba, Gerhard K. E.; Konjaria, Mari-Luiza; Krait, Sulaiman

doi:10.1002/9781119802280.ch8

Cited by 5 publications

(5 citation statements)

References 97 publications

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“…As stated in a recent work by Scriba et al, “it should be kept in mind that very often the selectors also display chemoselectivity because binding thermodynamics also differ for structurally related or unrelated compounds. Thus, chiral selectors may enable the simultaneous separation of stereoisomers and other compounds.” [ 89 ]. This assumption is supported by theoretical considerations as well as by experimental results.…”

Section: Discussionmentioning

confidence: 99%

Comprehensive Review on Chiral Stationary Phases in Single-Column Simultaneous Chiral–Achiral HPLC Separation Methods

Papp,

Szabó,

Hancu

et al. 2024

Molecules

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This comprehensive review explores the utilization of chiral stationary phases (CSPs) in the context of single-column simultaneous chiral–achiral high-performance liquid chromatography (HPLC) separation methods. While CSPs have traditionally been pivotal for enantioselective drug analysis, contemporary CSPs often exhibit notable chemoselective properties. Consequently, there is a discernible trend towards the development of methodologies that enable simultaneous enantio- and chemoselective separations utilizing a single CSP-based chromatographic column. This review provides an exhaustive overview of reported HPLC methods in this domain, with a focus on four major CSP types: cyclodextrin-, glycopeptide antibiotic-, protein-, and polysaccharide-based CSPs. This article delves into the diverse applications of CSPs, encompassing various chromatographic modes such as normal phase (NP), reverse phase (RP), and polar organic (PO). This review critically discusses method development, emphasizing the additional chemoselective separation mechanisms of CSPs. It also explores possibilities for method optimization and development, concluding with future perspectives on this evolving field. Despite the inherent challenges in understanding the retention mechanisms involved in chemoselective separations, this review highlights promising trends and anticipates a growing number of simultaneous enantio- and chemoselective methods in pharmaceutical analyses, pharmacokinetic studies, and environmental sample determinations.

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Section: Discussionmentioning

confidence: 99%

Comprehensive Review on Chiral Stationary Phases in Single-Column Simultaneous Chiral–Achiral HPLC Separation Methods

Papp,

Szabó,

Hancu

et al. 2024

Molecules

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“…17 Among various chiral selectors, cyclodextrins proved to be applicable for enantioseparation of various drugs, including illicit drugs and NPS. 18,19 Cyclodextrins are cyclic oligosaccharides made up of glucopyranose units building different ring sizes, namely α-cyclodextrins (six glucopyranose units), β-cyclodextrins (seven glucopyranose units) and γ-cyclodextrins (eight glucopyranose units). They can be used either immobilized or coated onto the stationary phase in gas chromatography (GC) 20 or HPLC columns 21,22 or as mobile phase additive in HPLC.…”

Section: Introductionmentioning

confidence: 99%

“…25 Their non-toxicity, low costs, the numerous possibilities for derivatization and the high solubility of many derivatives in water are advantageous. 19 Cyclodextrins are the most used chiral selectors for amphetamine derivatives and other NPS in CE. [26][27][28][29][30][31][32][33][34] T A B L E 1 Structures and names of investigated amphetamines.…”

Section: Introductionmentioning

confidence: 99%

“…Also, cyclodextrins are used as chiral additives in the background electrolyte in capillary electrophoresis (CE) 25 . Their non‐toxicity, low costs, the numerous possibilities for derivatization and the high solubility of many derivatives in water are advantageous 19 . Cyclodextrins are the most used chiral selectors for amphetamine derivatives and other NPS in CE 26–34 …”

Section: Introductionmentioning

confidence: 99%

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Screening of Astec® CHIRALDEX™ G‐PN and LIPODEX™ D gas chromatography columns for enantioseparation of amphetamine derivatives

Hubner,

Schützinger,

Molnárová

et al. 2024

Chirality

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Among different substance classes, New Psychoactive Substances (NPS) comprise chiral amphetamines for stimulant and empathic effects. There is little knowledge in terms of clinical studies about possibly different effects of the two enantiomers of novel amphetamine derivatives. For this reason, there is a big demand for enantioseparation method development of this new substance class.Regarding gas chromatography, cyclodextrins proved to be effective for enantioseparation of NPS. In our attempt, an Astec® Chiraldex™ G‐PN column containing 2,6‐di‐O‐pentyl‐3‐propionyl‐γ‐cyclodextrin and a Lipodex™ D column containing heptakis‐(2,6‐di‐O‐pentyl‐O‐acetyl)‐β‐cyclodextrin as chiral selector served as stationary phases in a Shimadzu GCMS‐QP2010 SE system.Because of the special coating, maximum temperature is limited to 200 °C isothermal or 220 °C in programmed mode. To ensure detection, trifluoroacetic anhydride (TFAA) was used to increase sample volatility.1 As a result, 35 amphetamines were tested as their TFAA‐derivatives.A screening method with a temperature gradient from 140 °C to 200 °C at a heating ramp of 1 °C per minute and final time of 5 min, showed baseline separation for seven and partial separations for 16 trifluoro acetylated amphetamines using the Chiraldex™ G‐PN column. Six baseline and nine partial separations were observed with the Lipodex™ D column, respectively.

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“…[8] The construction of well-defined chiral cavities allows for fine-tuning of chiral microenvironments, enabling chiral discrimination abilities that have attracted significant attention and extensive study. [9] While chiral macrocycles such as chiral crown ethers [10a] and cyclodextrins [10b-d] have been successfully commercialized and widely used in preparing chromatographic column packings for chiral separation, [11] there are still challenges to overcome. Firstly, the enantiomeric selectivity (α = K R(S) / K S(R) ) of most reported macrocyclic chiral receptors remains relatively low (α = 1-3), especially in the aqueous phase.…”

Section: Introductionmentioning

confidence: 99%

A Chiral Emissive Conjugated Corral for High‐Affinity and Highly Enantioselective Recognition in Water

Fu,

Zhao,

Han

et al. 2023

Angew Chem Int Ed

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Accurately distinguishing between enantiomeric molecules is a fundamental challenge in the field of chemistry. However, there is still significant room for improvement in both the enantiomeric selectivity (KR(S)/KS(R)) and binding strength of most reported macrocyclic chiral receptors to meet the demands of practical application scenarios. Herein, we synthesized a water‐soluble conjugated tubular host—namely, corral[4]BINOL—using a chiral 1,1′‐bi‐2‐naphthol (BINOL) derivative as the repeating unit. The conjugated chiral backbone endows corral[4]BINOL with good fluorescent emission (QY=34 % ) and circularly polarized luminescence (|glum| up to 1.4×10−3) in water. Notably, corral[4]BINOL exhibits high recognition affinity up to 8.6×1010 M−1 towards achiral guests in water, and manifested excellent enantioselectivity up to 18.7 towards chiral substrates, both of which represent the highest values observed among chiral macrocycles in aqueous solution. The ultrastrong binding strength, outstanding enantioselectivity, and facile accessibility, together with the superior fluorescent and chiroptical properties, endow corral[4]BINOL with great potential for a wide range of applications.

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Cyclodextrins

Cited by 5 publications

References 97 publications

Comprehensive Review on Chiral Stationary Phases in Single-Column Simultaneous Chiral–Achiral HPLC Separation Methods

Comprehensive Review on Chiral Stationary Phases in Single-Column Simultaneous Chiral–Achiral HPLC Separation Methods

Screening of Astec® CHIRALDEX™ G‐PN and LIPODEX™ D gas chromatography columns for enantioseparation of amphetamine derivatives

A Chiral Emissive Conjugated Corral for High‐Affinity and Highly Enantioselective Recognition in Water

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