Cyclodextrin clicked chiral stationary phases with functionalities-tuned enantioseparations in high performance liquid chromatography

Lin, Yuzhou; Zhou, Jie; Tang, Jian; Tang, Weihua

doi:10.1016/j.chroma.2015.06.051

Cited by 37 publications

(15 citation statements)

References 22 publications

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“…The optimized chiral resolutions for 17 racemates were compared with CCC2M5‐CSP (Table ). By varying the volume ratios of Hex/EtOH or Hex/IPA mobile phases, the enantioseparations of three flavonoids in Hex/EtOH (80/20, 70/30, 60/40, and 50/50) mobile phases were explored and compared with two CSPs . As we know, the addition of alcohol additives can result in increased retention of chiral eluents; on the one hand, it may worsen the enantioseparation on the other.…”

Section: Resultsmentioning

confidence: 99%

“…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. 20 We recently explored the perphenylcarbamate β-CD derived CSPs via azide-yne click reaction.…”

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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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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“…Generally, HPLC is the most frequently used technique for preparative separation [12][13][14][15]. But when the established NPLC method was scaled up into a high-throughput way, things became less efficient due to long analytical time (about 30 min), large solvent consumption (especially nonenvironmentally friendly solvent such as -hexane), and heavy solvent recovery work.…”

Section: Introductionmentioning

confidence: 99%

Improved Chiral Separation of (R,S)-Goitrin by SFC: An Application in Traditional Chinese Medicine

Nie

Dai

2016

Journal of Analytical Methods in Chemistry

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Like chemical drugs, research and development of herbal medicine also have a need to resolve enantiomers. To help illustrating the antiviral bioactivity of Isatidis Radix, a widely used traditional Chinese medicine (TCM), supercritical fluid chromatography (SFC) was used for analytical and preparative separation of (R,S)-goitrin, which was reported as the active ingredient of the herbal. Improved resolution was achieved on Chiralpak IC column, using acetonitrile as the organic modifier, representing a tenfold increase in speed, compared to the previous normal phase HPLC (NPLC) method. The newly developed chromatographic method was validated in terms of linearity, precision, limit of detection (LOD), and limit of quantitation (LOQ). Scale-up purification of (R)-goitrin and (S)-goitrin was performed on a preparative column with >90% total recovery. The absolute stereochemical assignment of the purified isomers was determined through optical rotation study. This attempt explored SFC's application in chiral research of traditional Chinese medicine.

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“…Benefitting from its special conformation, CDs have been widely used in many research areas such as chromatography, catalysis, drug delivery, water purification, and sensing [4,5,6,7,8]. By far, although there a large amount of CD functional materials have appeared, most of them are based on random substitution reactions on CD rims.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Click Access to a Cyclodextrin Dimer-Based Novel Aggregation Induced Emission Sensor and Monomer-Based Chiral Stationary Phase

Zhao

Tang

et al. 2016

Sensors

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A ‘two birds, one stone’ strategy was developed via a one-pot click reaction to simultaneously prepare a novel cyclodextrin (CD) dimer based aggregation induced emission (AIE) sensor (AIE-DCD) and a monomer based chiral stationary phase (CSP-MCD) for chiral high performance liquid chromatography (CHPLC). AIE-DCD was found to afford satisfactory AIE response for specific detection of Zn2+ with a detection limit of 50 nM. CSP-MCD exhibits excellent enantioseparation ability toward dansyl amino acids, where the resolution of dansyl amino leucine reaches 5.43.

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Cyclodextrin clicked chiral stationary phases with functionalities-tuned enantioseparations in high performance liquid chromatography

Cited by 37 publications

References 22 publications

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

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

Improved Chiral Separation of (R,S)-Goitrin by SFC: An Application in Traditional Chinese Medicine

One-Pot Click Access to a Cyclodextrin Dimer-Based Novel Aggregation Induced Emission Sensor and Monomer-Based Chiral Stationary Phase

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