8.10 Chromatographic Separations and Analysis: Cyclodextrin Mediated HPLC, GC and CE Enantiomeric Separations

Zhang, X.; Zhang, Y.; Armstrong, Daniel W.

doi:10.1016/b978-0-08-095167-6.00823-5

Cited by 16 publications

(12 citation statements)

References 176 publications

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“…The library of CSPs spans from Pirkle types to chiral crown ethers, macrocyclic glycopeptides antibiotics, ligand exchange, polysaccharides, proteins and cyclodextrins (CDs) 3 4 5 6 7 8 9 10 11 . CDs derived CSPs are advantageous for enantioseparation due to the versatile chemical modification to construct π-π interactions, dipole-dipole, ion-pairing, hydrogen bonding, electrostatic and steric repulsion interactions besides inclusion complexation to promote the chiral recognition process 12 13 . Moreover, CD CSPs are especially attractive for their compatibility and durability to be operated under different separation modes such as normal phase, reversed phase, polar organic and hydrophilic interaction modes.…”

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confidence: 99%

Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation

Tang

Zhang

Lin

et al. 2015

Sci Rep

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The separation of racemic molecules is of crucial significance not only for fundamental research but also for technical application. Enantiomers remain challenging to be separated owing to their identical physical and chemical properties in achiral environments. Chromatographic techniques employing chiral stationary phases (CSPs) have been developed as powerful tools for the chiral analysis and preparation of pure enantiomers, most of which are of biological and pharmaceutical interests. Here we report our efforts in developing high-performance phenylcarbamated cyclodextrin (CD) clicked CSPs. Insights on the impact of CD functionalities in structure design are provided. High-efficiency enantioseparation of a range of aryl alcohols and flavanoids with resolution values (Rs) over 10 were demonstrated by per(3-chloro-4-methyl)phenylcarbamated CD clicked CSP. Comparison study and molecular simulations suggest the improved enantioselectivity was attributed to higher interactions energy difference between the complexes of enantiomers and CSPs with phenylcarbamated CD bearing 3-chloro and 4-methyl functionalities.

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mentioning

confidence: 99%

Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation

Tang

Zhang

Lin

et al. 2015

Sci Rep

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“…HPLC‐grade trifluoroacetic acid (TFA) and triethylamine (TEA) were purchased from J&K (Shanghai, China). All racemates were procured from J&K. Two CSPs were prepared in our lab and packed into columns (4.6 × 250 mm) accordingly . Typically, 6 A –azido‐β‐cyclodextrin was functionalized by reacting with 4‐chloro‐3‐methylphenylisocyanate or 5‐chloro‐2‐methyl phenylisocyanate in dry pyridine.…”

Section: Methodsmentioning

confidence: 99%

“…All racemates were procured from J&K. Two CSPs were prepared in our lab and packed into columns (4.6 × 250 mm) accordingly. 15,18 Typically, 6 A -azido-β-cyclodextrin was functionalized by reacting with 4-chloro-3-methylphenylisocyanate or 5-chloro-2-methyl phenylisocyanate in dry pyridine. The CD derivatives were then clicked onto an alkynyl surfacemodified silica support to afford target CSPs.…”

Section: Methodsmentioning

confidence: 99%

“…High‐performance liquid chromatography (HPLC) has been employed as an important option for both chiral analysis and manufacturing by the use of chiral stationary phases (CSPs) . To date, chemically bonded cyclodextrins (CDs) CSPs have aroused prominent interest due to their practicality in different modes of HPLC . To form noncovalent “host–guest” inclusion complexes, CDs and their derivatives have found wide applications in drug delivery and enantioseparation.…”

Section: Introductionmentioning

confidence: 99%

“…[2][3][4][5][6][7][8][9][10][11][12][13] To date, chemically bonded cyclodextrins (CDs) CSPs have aroused prominent interest due to their practicality in different modes of HPLC. 14,15 To form noncovalent "host-guest" inclusion complexes, CDs and their derivatives have found wide applications in drug delivery and enantioseparation. The "click chemistry" 16 has recently evolved as a facile and efficient synthesis approach in the preparation of CSPs, [17][18][19][20][21][22] with thiol-ene clicked perphenylcarbamate β-CD CSP demonstrating good enantioselectivities in HPLC.…”

Section: Introductionmentioning

confidence: 99%

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Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

et al. 2017

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The mixed chloro- and methyl- functionalities can greatly modulate the enantioselectivities of phenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs). A comparison study is herein reported for per(4-chloro-3-methyl)phenylcarbamate and per(2-chloro-5-methyl)phenylcarbamate β-CD clicked CSPs (i.e., CCC4M3-CSP and CCC2M5-CSP). The enantioselectivity dependence on column temperature was studied in both normal-phase and reversed-phase mode high performance liquid chromatography (HPLC). The thermodynamic study revealed that the stronger intermolecular interactions can be formed between CCC4M3-CSP and chiral solutes to drive the chiral separation. The higher enantioselectivities of CCC4M3-CSP were further demonstrated with the enantioseparation of 17 model racemates in HPLC.

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ChiralGC

Schurig

2015

Analytical Separation Science

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In enantioselective gas chromatography (enantio‐GC), the chiral stationary phases (CSPs) are coated on deactivated capillary columns in bulk as nonvolatile liquids or as solution in a conventional achiral stationary phase (squalane, polyethylene glycol, and various polysiloxanes). In Chirasil‐type CSPs, the chiral selector is chemically bonded to a polysiloxane backbone and thermally immobilized on the capillary inner surface. Three different approaches of mixed binary selector systems in enantio‐GC have been described in this chapter. The separation of enantiomers on chiral nonracemic selectors by enantio‐GC is entirely governed by thermodynamics. It is brought about by the fast and reversible formation of transient and energetically distinct diastereomeric association complexes (DD′ and LD′) between the select and enantiomers (arbitrarily denoted D and L) and the enantiopure selector (arbitrarily denoted D′). The chapter ends with a note on the mechanisms of chirality recognition.

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8.10 Chromatographic Separations and Analysis: Cyclodextrin Mediated HPLC, GC and CE Enantiomeric Separations

Cited by 16 publications

References 176 publications

Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation

Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation

Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

ChiralGC

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