Separating and Identifying the Four Stereoisomers of Methyl Jasmonate by RP‐HPLC and using Cyclodextrins in a Novel Way

Matencio, Adrián; Bermejo-Gimeno, Mario J.; García-Carmona, Francisco; López‐Nicolás, José Manuel

doi:10.1002/pca.2654

Cited by 19 publications

(10 citation statements)

References 34 publications

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“…CD-containing chiral stationary phase (CSP) is extensively used in gas chromatography (GC), high-performance liquid chromatography (HPLC), thin-layer chromatography (TLC), micro solid phase extraction (μ-SPE), capillary electrophoresis (CE), capillary electrochromatography (CEC), electrokinetic chromatography (EKC), and supercritical fluid chromatography (SFC) for the separation of structurally similar compounds or complex product matrices of enantiomers [ 96 , 97 , 98 , 99 , 100 , 101 ]. The derivatization or coupling of CDs using various functional molecules is also widely employed in this field [ 102 , 103 , 104 , 105 , 106 , 107 , 108 , 109 , 110 , 111 , 112 ]. One such example can be seen in the study conducted by Sun et al, in which per-4-chlorophenylcarbamate/β-cyclodextrin-based CSP was developed and successfully applied for the separation of flurbiprofen enantiomers and 22 other drug racemates [ 109 , 110 ].…”

Section: Applications Of CD Inclusion Complexes In the Solid/solutmentioning

confidence: 99%

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Lee

2020

Molecules

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Cyclodextrins (CDs) have drawn a lot of attention from the scientific communities as a model system for host–guest chemistry and also due to its variety of applications in the pharmaceutical, cosmetic, food, textile, separation science, and essential oil industries. The formation of the inclusion complexes enables these applications in the condensed phases, which have been confirmed by nuclear magnetic resonance (NMR) spectroscopy, X-ray crystallography, and other methodologies. The advent of soft ionization techniques that can transfer the solution-phase noncovalent complexes to the gas phase has allowed for extensive examination of these complexes and provides valuable insight into the principles governing the formation of gaseous noncovalent complexes. As for the CDs’ host–guest chemistry in the gas phase, there has been a controversial issue as to whether noncovalent complexes are inclusion conformers reflecting the solution-phase structure of the complex or not. In this review, the basic principles governing CD’s host–guest complex formation will be described. Applications and structures of CDs in the condensed phases will also be presented. More importantly, the experimental and theoretical evidence supporting the two opposing views for the CD–guest structures in the gas phase will be intensively reviewed. These include data obtained via mass spectrometry, ion mobility measurements, infrared multiphoton dissociation (IRMPD) spectroscopy, and density functional theory (DFT) calculations.

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Section: Applications Of CD Inclusion Complexes In the Solid/solutmentioning

confidence: 99%

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Lee

2020

Molecules

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“…In the field of HPLC, Wang and co‐workers modelled the enantioseparation of flavonone with βCDs by MD, introducing the mixture MeOH/water 1:1 (RPLC conditions) as custom solvent . Starting from a different approach, López‐Nicolás and co‐workers modelled the contacts between methyl jasmonate stereoisomers and methyl‐βCD by molecular docking, as theoretical complement of the experimental enantioseparation performed by adding the selector to the MP, under RPLC conditions .…”

Section: Cyclodextrinsmentioning

confidence: 99%

Recent studies of docking and molecular dynamics simulation for liquid‐phase enantioseparations

et al. 2019

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Liquid‐phase enantioseparations have been fruitfully applied in several fields of science. Various applications along with technical and theoretical advancements contributed to increase significantly the knowledge in this area. Nowadays, chromatographic techniques, in particular HPLC on chiral stationary phase, are considered as mature technologies. In the last thirty years, CE has been also recognized as one of the most versatile technique for analytical scale separation of enantiomers. Despite the huge number of papers published in these fields, understanding mechanistic details of the stereoselective interaction between selector and selectand is still an open issue, in particular for high‐molecular weight chiral selectors like polysaccharide derivatives. With the ever growing improvement of computer facilities, hardware and software, computational techniques have become a basic tool in enantioseparation science. In this field, molecular docking and dynamics simulations proved to be extremely adaptable to model and visualize at molecular level the spatial proximity of interacting molecules in order to predict retention, selectivity, enantiomer elution order, and profile noncovalent interaction patterns underlying the recognition process. On this basis, topics and trends in using docking and molecular dynamics as theoretical complement of experimental LC and CE chiral separations are described herein. The basic concepts of these computational strategies and seminal studies performed over time are presented, with a specific focus on literature published between 2015 and November 2018. A systematic compilation of all published literature has not been attempted.

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“…Generally, CDs encapsulate poorly water-soluble compounds and hydrophobic moieties of amphiphilic molecules. Nevertheless, the solubility of these complexes not only depends on the CD used but also on different factors such as pH or guess molecule [5][6][7][8]. The capacity of CDs to increase solubility and protect several molecules has increased their use in the pharmaceutical and food industries [1,9,10].…”

Section: Introductionmentioning

confidence: 99%

Strategies to Develop Cyclodextrin-Based Nanosponges for Smart Drug Delivery

Hoti¹,

Appleton²,

Pedrazzo³

et al. 2022

Smart Drug Delivery

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In recent years, the development of various cyclodextrin (CD)-based nanosponges (NSs) has gained great importance in the controlled and-or targeted release of drugs due to their versatility and simple preparation. In this chapter, an introduction of different administration routes is explained. Further, different ways to obtain CD-NSs and their classification are shown with a brief explanation of the characterization of the inclusion complexes. Finally, illustrative examples in diverse processes or diseases will be reviewed and explained to demonstrate the potential of CD-NSs. Therefore, this division will serve to compile information on CD-NSs in recent years and to illustrate to readers how to generate and apply different derivatives of interest.

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Separating and Identifying the Four Stereoisomers of Methyl Jasmonate by RP‐HPLC and using Cyclodextrins in a Novel Way

Abstract: The new method identified and classified the four stereoisomers of MeJA in the following ordination: (-)epiMeJA, (-)MeJA; (+)MeJA and (+)epiMeJA. These results could be used to improve the elicitation of cell cultures with only the best isomer. Copyright © 2016 John Wiley & Sons, Ltd.

Cited by 19 publications

References 34 publications

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Recent studies of docking and molecular dynamics simulation for liquid‐phase enantioseparations

Strategies to Develop Cyclodextrin-Based Nanosponges for Smart Drug Delivery

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