Enantioseparation characteristics of biselector chiral stationary phases based on derivatives of cellulose and amylose

Wang, Zhao-Qun; Liu, Jian-De; Chen, Wei; Bai, Zheng‐Wu

doi:10.1016/j.chroma.2014.04.044

Cited by 25 publications

(13 citation statements)

References 27 publications

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“…As well known, coated‐type CSPs have excellent chiral resolution performance, but can only be used in rather restricted mobile phase condition, which limited the application of coated‐type CSPs. In order to overcome the defect, Bai and coworkers prepared a series of biselector coated‐type CSPs to improve chiral resolution ability, solvent resistance, and durability of CSPs . Wang et al developed biselector CSPs based on derivatives of cellulose and amylose that had powerful enantioseparation capability.…”

Section: Introductionmentioning

confidence: 99%

“…Wang et al developed biselector CSPs based on derivatives of cellulose and amylose that had powerful enantioseparation capability. Moreover, the prepared biselector CSPs could work in a mobile phase of high ethanol ratio and have good durability . Zhang et al synthesized biselector CSPs based on amylose and chitin derivatives, which the stability and solvent tolerance were obviously improved .…”

Section: Introductionmentioning

confidence: 99%

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Preparation and evaluation of biselector bonded‐type multifunctional chiral stationary phase based on dialdehyde cellulose and 6‐monodeoxy‐6‐monoamino‐β‐cyclodextrine derivatives

Gao

Quan

et al. 2020

Chirality

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A novel biselector bonded‐type multifunctional chiral stationary phase (MCSP) was prepared by covalently crosslinking dialdehyde cellulose (DAC) with 6‐monodeoxy‐6‐monoamino‐β‐cyclodextrine (CD) via Schiff base reaction. The biselector bonded‐type MCSP had good chiral and achiral chromatographic performance in normal phase (NP) and reversed phase (RP) modes. Seven and eight enantiomers were successfully separated on the prepared biselector bonded‐type MCSP in NP and RP modes, respectively. The biselector bonded‐type MCSP showed enhanced chiral resolution ability compared with single selector chiral stationary phases due to the simultaneous introduction of DAC and 6‐monodeoxy‐6‐monoamino‐β‐CD on the surface of silica gel. Aromatic compounds including polycyclic aromatic hydrocarbons, anilines, phenols, phenylates, and aromatic acids were choosed as analytes to investigate the achiral chromatographic performance of the biselector bonded‐type MCSP in NP and RP modes. Chromatographic evaluation results showed that the above aromatic compounds were essentially capable of achieving baseline separation by hydrophobic interaction, π‐π interaction, and π‐π electron‐donor‐acceptor interaction. Moreover, the host‐guest inclusion effect of 6‐monodeoxy‐6‐monoamino‐β‐CD and the multiple interactions made the biselector bonded‐type MCSP have good steric selectivity. The preparation method of the biselector bonded‐type MCSP was simple and provided a new idea and strategy for the preparation of the subsequent novel biselector MCSP.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation and evaluation of biselector bonded‐type multifunctional chiral stationary phase based on dialdehyde cellulose and 6‐monodeoxy‐6‐monoamino‐β‐cyclodextrine derivatives

Gao

Quan

et al. 2020

Chirality

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“…The suspensions were sonicated to form slurries, and then were packed into empty stainless-steel columns with n-hexane as the displacer solvent [7]. The columns of CSPa and CSPb were packed with the same way.…”

Section: Column Packing and Chromatographymentioning

confidence: 99%

“…The re-precipitation was processed three times and the product was washed with methanol and water in sequence. The purified derivative was dried in vacuum, and 1.70 g of chitosan bis (4- CSPb, respectively) were prepared in our previous work with the same support and coating method to prepare CSPs1-6 [7]. ADMPC and CDMPC were also fed at a ratio of 20% by weight.…”

Section: Preparation Of Chitosan Isobutyrylamide Derivatives and Cspsmentioning

confidence: 99%

“…Among the various CSPs, which have been developed for HPLC, polysaccharide-derived CSPs, especially those based on cellulose and amylose derivatives, have been most extensively studied and played significant roles in enantioseparation [6][7][8][9][10]. racemates that were equal to or even higher than those of cellulose or amylose derivatives based CSPs.…”

Section: Introductionmentioning

confidence: 99%

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Chiral stationary phases based on chitosan bis(methylphenylcarbamate)-(isobutyrylamide) for high-performance liquid chromatography

Tang

Qin

Chen

et al. 2016

Journal of Chromatography A

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a b s t r a c tA series of chitosan bis(methylphenylcarbamate)-(isobutyrylamide) derivatives were synthesized by carbamylating chitosan isobutyrylamide with different methylphenyl isocyanates. Then the prepared chitosan derivatives were coated onto 3-aminopropyl silica particles, resulting in a series of new chiral stationary phases (CSPs) for high-performance liquid chromatography. It was observed that the chiral recognition abilities of these coated-type CSPs depended very much on the substituents on the phenyl moieties of the chitosan derivatives, the eluent composition, as well as the structure of racemates. As a typical example, the eluent tolerance of the prepared CSP with the best enantioseparation ability was investigated in detail, and the results revealed that the CSP exhibited extraordinary solvent tolerance and could still work without significant loss in enantioseparation capability after being flushed with chloroform (100%), ethyl acetate (100%) and even THF/n-hexane (70/30, v/v), while the traditional coated-type CSPs based on the cellulose and amylose derivatives, such as cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) and amylose tris(3,5-dimethylphenylcarbamate) (ADMPC), might be dissolved or highly swollen in these eluents. Therefore, the application of the resultant CSPs could address the problem of the dissolution and high swelling of traditional coated-type CSPs in some unusual eluents, broadening the possibility of eluent choice. In addition, a comparison of the prepared CSPs with the well known CDMPC-and ADMPC-based CSPs concerning the chiral recognition ability was also made. Separation performances achieved on the as-prepared CSPs in different eluents were found to be even superior to CDMPC-and ADMPC-based CSPs for the tested chiral compounds. In summary, we could safely draw the conclusion that the CSPs derived from chitosan isobutyrylamide derivatives were capable of excellent chiral recognition ability, and meanwhile possessed satisfactory eluent tolerance in a wider range of solvents.

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Fundamentals of chirality, resolution, and enantiopure molecule synthesis methods

2022

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The chirality of molecules is a concept that explains the interactions in nature. We may observe the same formula but different organizations revolving around the chiral center. Since Pasteur's meticulous observation of sodium ammonium tartrate crystals' structure, scientists have discovered many features of chiral molecules. The number of newly approved single enantiomeric drugs increases every year and takes place in the market. Thus, separation or resolution methods of racemic mixtures are of continued importance in the efficacy of drugs, installation of affordable production processes, and convenient synthetic chemistry practice. This article presents the asymmetric synthesis approaches and the classification of direct resolution methods of chiral molecules.

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Enantioseparation characteristics of biselector chiral stationary phases based on derivatives of cellulose and amylose

Cited by 25 publications

References 27 publications

Preparation and evaluation of biselector bonded‐type multifunctional chiral stationary phase based on dialdehyde cellulose and 6‐monodeoxy‐6‐monoamino‐β‐cyclodextrine derivatives

Preparation and evaluation of biselector bonded‐type multifunctional chiral stationary phase based on dialdehyde cellulose and 6‐monodeoxy‐6‐monoamino‐β‐cyclodextrine derivatives

Chiral stationary phases based on chitosan bis(methylphenylcarbamate)-(isobutyrylamide) for high-performance liquid chromatography

Fundamentals of chirality, resolution, and enantiopure molecule synthesis methods

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