Synthesis and enantioseparation characteristics of a novel mono-6-deoxy-(2,4-dihydroxybenzimide)-β-cyclodextrin as a chiral stationary phase in high-performance liquid chromatography

Xia Li; Zhiming Zhou; Li Dai; Wenhong Zhou; Jinliang Wang

doi:10.1016/j.talanta.2011.09.006

Synthesis and enantioseparation characteristics of a novel mono-6-deoxy-(2,4-dihydroxybenzimide)-β-cyclodextrin as a chiral stationary phase in high-performance liquid chromatography

Xia Li, Zhiming Zhou^*, Li Dai, Wenhong Zhou, Jinliang Wang

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

Abstract

A novel chiral selector mono-6-deoxy-(2,4-dihydroxybenzimide)-β-CD (MDHB-β-CD) in which the derivatized group and the cavity of CD is linked by CH₂-NC group, was successfully prepared, and the structural characteristics were determined by FT-IR, ¹H and ¹³C NMR, MALDITOF-MS and element analysis. The corresponding stationary phase (CSP) was used in HPLC and the enantioseparation performance was investigated using chiral 1-phenyl-2-nitroethanol derivatives as test samples in the reverse-phase mode composed of methanol/water and acetonitrile/TEAA. Better separation abilities and excellent enantioselectivities (α > 1.26, R_S > 1.73) were obtained on MDHB-β-CD CSP for these chiral compounds in the methanol/water mobile phase.

Original language	English
Pages (from-to)	452-456
Number of pages	5
Journal	Talanta
Volume	86
Issue number	1
DOIs	https://doi.org/10.1016/j.talanta.2011.09.006
Publication status	Published - 30 Oct 2011

Keywords

Chiral compounds
Cyclodextrin derivative
Enantioseparation
High-performance liquid chromatography
Stationary phase

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10.1016/j.talanta.2011.09.006

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title = "Synthesis and enantioseparation characteristics of a novel mono-6-deoxy-(2,4-dihydroxybenzimide)-β-cyclodextrin as a chiral stationary phase in high-performance liquid chromatography",

abstract = "A novel chiral selector mono-6-deoxy-(2,4-dihydroxybenzimide)-β-CD (MDHB-β-CD) in which the derivatized group and the cavity of CD is linked by CH2-NC group, was successfully prepared, and the structural characteristics were determined by FT-IR, 1H and 13C NMR, MALDITOF-MS and element analysis. The corresponding stationary phase (CSP) was used in HPLC and the enantioseparation performance was investigated using chiral 1-phenyl-2-nitroethanol derivatives as test samples in the reverse-phase mode composed of methanol/water and acetonitrile/TEAA. Better separation abilities and excellent enantioselectivities (α > 1.26, RS > 1.73) were obtained on MDHB-β-CD CSP for these chiral compounds in the methanol/water mobile phase.",

keywords = "Chiral compounds, Cyclodextrin derivative, Enantioseparation, High-performance liquid chromatography, Stationary phase",

author = "Xia Li and Zhiming Zhou and Li Dai and Wenhong Zhou and Jinliang Wang",

year = "2011",

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doi = "10.1016/j.talanta.2011.09.006",

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T1 - Synthesis and enantioseparation characteristics of a novel mono-6-deoxy-(2,4-dihydroxybenzimide)-β-cyclodextrin as a chiral stationary phase in high-performance liquid chromatography

AU - Li, Xia

AU - Zhou, Zhiming

AU - Dai, Li

AU - Zhou, Wenhong

AU - Wang, Jinliang

PY - 2011/10/30

Y1 - 2011/10/30

N2 - A novel chiral selector mono-6-deoxy-(2,4-dihydroxybenzimide)-β-CD (MDHB-β-CD) in which the derivatized group and the cavity of CD is linked by CH2-NC group, was successfully prepared, and the structural characteristics were determined by FT-IR, 1H and 13C NMR, MALDITOF-MS and element analysis. The corresponding stationary phase (CSP) was used in HPLC and the enantioseparation performance was investigated using chiral 1-phenyl-2-nitroethanol derivatives as test samples in the reverse-phase mode composed of methanol/water and acetonitrile/TEAA. Better separation abilities and excellent enantioselectivities (α > 1.26, RS > 1.73) were obtained on MDHB-β-CD CSP for these chiral compounds in the methanol/water mobile phase.

AB - A novel chiral selector mono-6-deoxy-(2,4-dihydroxybenzimide)-β-CD (MDHB-β-CD) in which the derivatized group and the cavity of CD is linked by CH2-NC group, was successfully prepared, and the structural characteristics were determined by FT-IR, 1H and 13C NMR, MALDITOF-MS and element analysis. The corresponding stationary phase (CSP) was used in HPLC and the enantioseparation performance was investigated using chiral 1-phenyl-2-nitroethanol derivatives as test samples in the reverse-phase mode composed of methanol/water and acetonitrile/TEAA. Better separation abilities and excellent enantioselectivities (α > 1.26, RS > 1.73) were obtained on MDHB-β-CD CSP for these chiral compounds in the methanol/water mobile phase.

KW - Chiral compounds

KW - Cyclodextrin derivative

KW - Enantioseparation

KW - High-performance liquid chromatography

KW - Stationary phase

UR - https://www.scopus.com/pages/publications/80755153023

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DO - 10.1016/j.talanta.2011.09.006

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AN - SCOPUS:80755153023

SN - 0039-9140

VL - 86

SP - 452

EP - 456

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IS - 1

ER -

Synthesis and enantioseparation characteristics of a novel mono-6-deoxy-(2,4-dihydroxybenzimide)-β-cyclodextrin as a chiral stationary phase in high-performance liquid chromatography

Abstract

Keywords

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