Dependence of enantioseparation performance on structure of chiral selectors derived from N-cycloalkylcarbonyl chitosan

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

doi:10.1016/j.reactfunctpolym.2019.04.022

Cited by 12 publications

(7 citation statements)

References 53 publications

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“…In another approach, N-cyclopentylcarbonyl chitosan derivatives, comprising ten 3,6bis-(arylcarbamate)-2-(cyclopentylformamide) derivatives with different substituents at the phenyl moiety, were synthesized by Fu et al [63] (Figure 5). Tröger's base, 2-phenylchroman-…”

Section: Chitosan-based Cspsmentioning

confidence: 99%

“…In another approach, N -cyclopentylcarbonyl chitosan derivatives, comprising ten 3,6- bis -(arylcarbamate)-2-(cyclopentylformamide) derivatives with different substituents at the phenyl moiety, were synthesized by Fu et al [ 63 ] ( Figure 5 ). Tröger’s base, 2-phenylchroman-4-one, 1-(2-napthyl)-ethanol, methyl phenyl sulfoxide, 1-phenylethanol, mephobarbital, 4-phenyloxazolidin-2-one, 1-(1-phenylethyl)-3-(3-p-tolyl)urea, 1-(2,4-dichlorophenyl)-2-(1 H -imidazol-1-yl)ethanol, 4-methyl- N -(1-phenylethyl)benzamide, benzoin, 1-(1-(4-methoxyphenyl)ethyl)-3-phenylurea, aminoglutethimide, glutethimide, citalopram hydrobromide, efavirenz, N -(1-(4-methoxyphenyl)ethyl)-3,5-dinitobenzamide, omeprazole sodium, 4-(4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, and voriconazole were employed as the analytes to evaluate the ES performance of the chitosan-based CSs.…”

Section: Chitosan-based Cspsmentioning

confidence: 99%

“… Chemical structures of different chitosan 3,6- bis -(aryl carbamate)-2-( N -cyclopentylcarbonyl) derivative-based CSs synthesized by Fu et al [ 63 ]. …”

Section: Figurementioning

confidence: 99%

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Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Bui

Rosenau

2021

Molecules

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Polysaccharides, oligosaccharides, and their derivatives, particularly of amylose, cellulose, chitosan, and β-cyclodextrin, are well-known chiral selectors (CSs) of chiral stationary phases (CSPs) in chromatography, because they can separate a wide range of enantiomers. Typically, such CSPs are prepared by physically coating, or chemically immobilizing the polysaccharide and β-cyclodextrin derivatives onto inert silica gel carriers as chromatographic support. Over the past few years, new chiral selectors have been introduced, and progressive methods to prepare CSPs have been exploited. Also, chiral recognition mechanisms, which play a crucial role in the investigation of chiral separations, have been better elucidated. Further insights into the broad functional performance of commercially available chiral column materials and/or the respective newly developed chiral phase materials on enantiomeric separation (ES) have been gained. This review summarizes the recent developments in CSs, CSP preparation, chiral recognition mechanisms, and enantiomeric separation methods, based on polysaccharides and β-cyclodextrins as CSs, with a focus on the years 2019–2020 of this rapidly developing field.

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Section: Chitosan-based Cspsmentioning

confidence: 99%

Section: Chitosan-based Cspsmentioning

confidence: 99%

See 1 more Smart Citation

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Bui

Rosenau

2021

Molecules

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show abstract

“…[30][31][32][33] Besides, influences of chitosan source and structure of chitosan derivatives on enantioseparation capability were studied. [34][35][36] In summary, relative to cellulose/amylose-based CSPs, some developed chitosan-based CSPs also have high enantioseparation capability for chiral compounds, and are highly tolerable against eluents containing a "unusual solvent". Thus, chitosan-based CSPs are competitive in practical application.…”

Section: Introductionmentioning

confidence: 99%

“…In a word, the phenyl group plays an important role for enantioseparation. However, in many chitosan-based CSs reported in literature, substituents attached to functional groups at 2-position were an alkyl group rather than a phenyl group, [29][30][31][32][33][34][35][36] and a number of corresponding CSPs also showed a high enantioseparation capability. Thus, an issue arises that is, how many phenyl groups in one glucosamine are necessary for a chitosan-based CS with a satisfactory enantioseparation performance.…”

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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Further insight for the synthesis of 6‐amino‐6‐deoxy amylose

Zhang

Shan

Liu

et al. 2020

J of Applied Polymer Sci

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Because 6-amino-6-deoxy amylose is an important intermediate for many materials, developing a practical pathway to easily prepare it in bulk is of significance. The synthesis of 6-amino-6-deoxy amylose included three reactions. In the chlorination reaction, the crude product could be fully de-esterified under the improved conditions, and the reaction mechanism was re-understood. The azido group was reduced with sodium borohydride in which the reaction conditions were studied in detail. With the improved synthetic pathway, 6-amino-6-deoxy amylose could be easily prepared. The 6-amino-6-deoxy amylose was characterized via its benzamide derivative with 1 H NMR, 1 H-13 C HSQC NMR, and 1 H-1 H COSY NMR, confirming the hydroxyl group at C 6 of amylose was converted to amino group with a degree of substitution of 98.2%. Additionally, the 6-amino-6-deoxy amylose was analyzed toward iodine reagent and X-ray diffraction, and the corresponding results showed that it was different from amylose in suprastructure and crystal structure.

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Dependence of enantioseparation performance on structure of chiral selectors derived from N-cycloalkylcarbonyl chitosan

Cited by 12 publications

References 53 publications

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

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

Further insight for the synthesis of 6‐amino‐6‐deoxy amylose

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