Structure screening and performance restoration of chiral separation materials based on chitosan derivatives

Fu, Ke-Qin; Xi, Jiangbo; Chen, Wei; Tang, Sheng; Bai, Zheng‐Wu

doi:10.1016/j.carbpol.2019.03.031

Cited by 17 publications

(6 citation statements)

References 42 publications

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“…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%

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: Introductionmentioning

confidence: 99%

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

Gao

Zhang

et al. 2021

Chirality

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“…This technique is based on the chiral recognition ability of chiral stationary phases (CSPs) . In spite of polysaccharide‐based CSPs that showed good chiral separation abilities for varies of enantiomers, synthetic helical polymers, especially poly(phenylacetylene) derivatives, have also been widely investigated by researchers around the world because of their specific architectures …”

Section: Introductionmentioning

confidence: 99%

“…But the preparation method of immobilized‐type CSPs was not convenient enough than the coated‐type CSPs. To the best of our knowledge, only some coated‐type CSPs based on chitosan derivatives had been reported for using those polar solvents in eluent in HPLC . In this study, two novel poly(phenylacetylene) derivatives ( PPA‐S and PPA‐R ) containing stereomeric phenylethyl carbamate residues in the end of each side chain were designed and synthesized.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of poly(phenylacetylene)s containing chiral phenylethyl carbamate residues as coated‐type CSPs with high solvent tolerability

et al. 2020

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Two novel helical poly(phenylacetylene) derivatives containing chiral phenylethyl carbamate residues in the end of each side chain (PPA-S and PPA-R) were synthesized by polymerization of the corresponding phenylacetylene monomers using Rh(nbd)BPh 4 as a catalyst in DMF. The enantioseparation properties of the polymers were evaluated as coated-type chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). Under the same chromatographic conditions, PPA-S and PPA-R showed different enantioseparation properties, indicating that the different interactions between the analytes and the polymers, which result from the different chiral phenylethyl carbamate groups in the end of each side chains.Racemates 1, 7, and 8 could be better resolved on PPA-S, while racemate 6 was separated on PPA-R more efficiently. In addition, the coated-type CSPs showed good solvent tolerability and could work without any damage by introducing the polar solvents, such as CHCl 3 and THF, in eluent. Moreover, some racemates could be better resolved on these coated-type CSPs with the addition of THF to the eluent. K E Y W O R D S chiral phenylethyl carbamate, CSP, enantioseparation, helical poly(phenylacetylene), HPLC, solvent tolerability

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“…23 The use of polysaccharide derivatives such as amylose and cellulose, coated or immobilized on silica gel, as chiral selectors proved their efficiency in chiral separation of racemic compounds. 19,[24][25][26][27] The mechanism of chiral recognition by these CSPs at a molecular level is still obscure due to the complexity of their structures. 25 Even though certain rationales for enantiomer separation by HPLC are known, no theory exists that allows for the prediction of separation results and enantiomer elution order based on analyte structure, mobile phase composition, and stationary phase chiral selector.…”

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confidence: 99%

Enantioseparation and antioxidant activity of novel diarylpyrazoline derivatives

et al. 2022

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Three chiral pyrazoline derivatives were synthesized by a flavanone ring‐opening reaction followed by cyclocondensation with hydrazine hydrate to give better yields. Their enantiomeric resolution was achieved using polysaccharide chiral stationary phase columns consisting of cellulose (Chiralcel®OD‐RH, Chiralcel®OZ‐3) and amylose (Chiralpak®IA) by high‐performance liquid chromatography. The separation was affected by the nature and concentration of the alcohol modifiers in the mobile phase. Taking 5‐methoxy‐2‐(3‐phenyl‐4,5‐dihydro‐1H‐pyrazol‐5‐yl)phenol (3a) as an example, the best separation was obtained by using the Chiralpak®IA column, with a separation factor α = 1.24 and Rs = 5.66 within an analysis time of <30 min. The diarylpyrazolines showed good antioxidant activity, studied by the DPPH method.

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Structure screening and performance restoration of chiral separation materials based on chitosan derivatives

Cited by 17 publications

References 42 publications

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

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

Synthesis of poly(phenylacetylene)s containing chiral phenylethyl carbamate residues as coated‐type CSPs with high solvent tolerability

Enantioseparation and antioxidant activity of novel diarylpyrazoline derivatives

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