Enantioseparation using chitosan 2-isopropylthiourea-3,6-dicarbamate derivatives as chiral stationary phases for high-performance liquid chromatography

Zhang, Lili; Deng, Hongzhong; Wu, Xuepeng; Gao, Hanyuan; Shen, Jun; Cao, Huaqi; Qiao, Yingjie

doi:10.1016/j.chroma.2020.461174

Cited by 17 publications

(7 citation statements)

References 37 publications

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“…The enantioseparations were confirmed by UV spectrum of two separated enantiomers which presented the same spectrum profile. The chiral analytes were also employed in previous studies reported in literature, 11,27,30,34 and some of them are drugs or intermediates of drugs. The chromatographic results are presented in Tables 2 and 3.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, many coated‐type CSPs of chitosan derivatives were reported, and some of them possessed high enantioseparation capability and high tolerability towards mobile phases 27–30 . These CSPs could work in mobile phases with ethyl acetate, acetone, and even tetrahydrofuran as additives, which were prohibited for coated‐type CSPs of cellulose/amylose derivatives 31–34 .…”

Section: Introductionmentioning

confidence: 99%

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Chiral separation materials based on derivatives of 6‐amino‐6‐deoxyamylose

Gao

Zhang

et al. 2021

Chirality

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In order to develop new type of chiral separation materials, in this study, 6‐amino‐6‐deoxyamylose was used as chiral starting material with which 10 derivatives were synthesized. The amino group in 6‐amino‐6‐deoxyamylose was selectively acylated and then the hydroxyl groups were carbamoylated yielding amylose 6‐amido‐6‐deoxy‐2,3‐bis(phenylcarbamate)s, which were employed as chiral selectors (CSs) for chiral stationary phases of high‐performance liquid chromatography. The resulted 6‐amido‐6‐deoxyamyloses and amylose 6‐amido‐6‐deoxy‐2,3‐bis(phenylcarbamate)s were characterized by IR, 1H NMR, and elemental analysis. Enantioseparation evaluations indicated that most of the CSs demonstrated a moderate chiral recognition capability. The 6‐nonphenyl (6‐nonPh) CS of amylose 6‐cyclohexylformamido‐6‐deoxy‐2,3‐bis(3,5‐dimethylphenylcarbamate) showed the highest enantioselectivity towards the tested chiral analytes; the phenyl‐heterogeneous (Ph‐hetero) CS of amylose 6‐(4‐methylbenzamido)‐6‐deoxy‐2,3‐bis(3,5‐dimethylphenylcarbamate) baseline separated the most chiral analytes; the phenyl‐homogeneous (Ph‐homo) CS of amylose 6‐(3,5‐dimethylbenzamido)‐6‐deoxy‐2,3‐bis(3,5‐dimethylphenylcarbamate) also exhibited a good enantioseparation capability among the developed CSs. Regarding Ph‐hetero CSs, the enantioselectivity depended on the combination of the substituent at 6‐position and that at 2‐ and 3‐positions; as for Ph‐homo CSs, the enantioselectivity was related to the substituent at 2‐, 3‐, and 6‐positions; with respect to 6‐nonPh CSs, the retention factor of most analytes on the corresponding CSPs was lower than that on Ph‐hetero and Ph‐homo CSPs in the same mobile phases, indicating π–π interactions did occur during enantioseparation. Although the substituent at 6‐position could not provide π–π interactions, the 6‐nonPh CSs demonstrated an equivalent or even higher enantioselectivity compared with the Ph‐homo and Ph‐hetero CSs.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chiral separation materials based on derivatives of 6‐amino‐6‐deoxyamylose

Gao

Zhang

et al. 2021

Chirality

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“…New derivatives of chitosan with isopropylthiourea and carbamate groups were coated onto 3-aminopropyl silanized silica gel by Okamoto et col. [ 38 ]. Comparing the enantioseparation performance of chitosan 2-isopropylthiourea derivatives with the commercial CSP CHIRALCEL OD ® and chitosan derivatives with substituents at position 2, the new CSPs demonstrated a higher enantioselectivity and resolution for some racemates.…”

Section: Coating Methodsmentioning

confidence: 99%

“…Comparing the enantioseparation performance of chitosan 2-isopropylthiourea derivatives with the commercial CSP CHIRALCEL OD ® and chitosan derivatives with substituents at position 2, the new CSPs demonstrated a higher enantioselectivity and resolution for some racemates. CSPs were characterized by NMR, FTIR, elemental analysis and TGA [ 38 ].…”

Section: Coating Methodsmentioning

confidence: 99%

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

et al. 2021

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Enantioselective chromatography is one of the most used techniques for the separation and purification of enantiomers. The most important issue for a specific successful enantioseparation is the selection of the suitable chiral stationary phase (CSP). Different synthetic approaches have been applied for the preparation of CSPs, which embrace coating and immobilization methods. In addition to the classical and broadly applied coating and immobilization procedures, innovating strategies have been introduced recently. In this review, an overview of different methods for the preparation of coated and immobilized CSPs is described. Updated examples of CSPs associated with the various strategies are presented. Considering that after the preparation of a CSP its characterization is fundamental, the methods used for the characterization of all the described CSPs are emphasized.

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“…[22][23][24][25] Okamoto and coworkers developed C 2 -imide/urea (an imido/ ureido group on 2-position of chitosan) CSPs, and some of the CSPs exhibited strong enantioseparation. [26][27][28] They found chitosan-based CSPs could work in eluents in the presence of ethyl acetate and chloroform, which were called "unusual solvent" for cellulose/amylose-based CSPs. In recent years, we synthesized many chitosan derivatives with which corresponding CSPs were prepared, and a number of the chitosan-based CSPs demonstrated high enantioseparation capability and high tolerability to eluents.…”

Section: Introductionmentioning

confidence: 99%

Influence of phenyl group number on enantioseparation performance of chitosan‐based materials

Chen

Wang

Qiu

et al. 2020

J of Applied Polymer Sci

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In order to investigate the influence of phenyl group number on enantioseparation capability of a chitosan-based chiral selector (CS), in this study, two series of chitosan derivative and their enantioseparation were presented. According to the functional group at 2-position of glucosamine, the derivatives were classified as amido-type and ureido-type. In the amido-type CSs, the CS with two phenyl groups showed the best enantioseparation capability; the CS with one phenyl group exhibited the poorest enantioseparation; and the enantioseparation performance of the CS with three phenyl groups intermediated between those of the CSs with one and two phenyl groups. In the ureido-type, the CS bearing three phenyl groups was in the middle of two CSs with two phenyl groups in enantioseparation capability. Based on the results obtained in the present study, one phenyl group in a chitosan derivative is not enough for enantioseparation, and two or three phenyl groups are necessary. On the other hand, introducing three phenyl groups onto one glucosamine unit of chitosan, can not definitely result in a better enantioseparation capability, comparing with introducing two phenyl groups.

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Enantioseparation using chitosan 2-isopropylthiourea-3,6-dicarbamate derivatives as chiral stationary phases for high-performance liquid chromatography

Cited by 17 publications

References 37 publications

Chiral separation materials based on derivatives of 6‐amino‐6‐deoxyamylose

Chiral separation materials based on derivatives of 6‐amino‐6‐deoxyamylose

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

Influence of phenyl group number on enantioseparation performance of chitosan‐based materials

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