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Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety.
Chirality. 2020 08; 32(8):1080-1090.C

Abstract

Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.

Authors+Show Affiliations

Engineering Research Center of Pharmaceutical Process Chemistry, School of Pharmacy, Ministry of Education, East China University of Science and Technology, Shanghai, China.Engineering Research Center of Pharmaceutical Process Chemistry, School of Pharmacy, Ministry of Education, East China University of Science and Technology, Shanghai, China.Engineering Research Center of Pharmaceutical Process Chemistry, School of Pharmacy, Ministry of Education, East China University of Science and Technology, Shanghai, China.Engineering Research Center of Pharmaceutical Process Chemistry, School of Pharmacy, Ministry of Education, East China University of Science and Technology, Shanghai, China.Engineering Research Center of Pharmaceutical Process Chemistry, School of Pharmacy, Ministry of Education, East China University of Science and Technology, Shanghai, China.Engineering Research Center of Pharmaceutical Process Chemistry, School of Pharmacy, Ministry of Education, East China University of Science and Technology, Shanghai, China.Engineering Research Center of Pharmaceutical Process Chemistry, School of Pharmacy, Ministry of Education, East China University of Science and Technology, Shanghai, China.Engineering Research Center of Pharmaceutical Process Chemistry, School of Pharmacy, Ministry of Education, East China University of Science and Technology, Shanghai, China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32383525

Citation

Zhu, Lunan, et al. "Novel Chiral Stationary Phases Based On 3,5-dimethyl Phenylcarbamoylated Β-cyclodextrin Combining Cinchona Alkaloid Moiety." Chirality, vol. 32, no. 8, 2020, pp. 1080-1090.
Zhu L, Zhu J, Sun X, et al. Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety. Chirality. 2020;32(8):1080-1090.
Zhu, L., Zhu, J., Sun, X., Wu, Y., Wang, H., Cheng, L., Shen, J., & Ke, Y. (2020). Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety. Chirality, 32(8), 1080-1090. https://doi.org/10.1002/chir.23237
Zhu L, et al. Novel Chiral Stationary Phases Based On 3,5-dimethyl Phenylcarbamoylated Β-cyclodextrin Combining Cinchona Alkaloid Moiety. Chirality. 2020;32(8):1080-1090. PubMed PMID: 32383525.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety. AU - Zhu,Lunan, AU - Zhu,Junchen, AU - Sun,Xiaotong, AU - Wu,Yaling, AU - Wang,Huiying, AU - Cheng,Lingping, AU - Shen,Jiawei, AU - Ke,Yanxiong, Y1 - 2020/05/08/ PY - 2020/02/19/received PY - 2020/04/02/revised PY - 2020/04/20/accepted PY - 2020/5/10/pubmed PY - 2020/5/10/medline PY - 2020/5/9/entrez KW - HPLC KW - chiral stationary phases KW - cinchona alkaloid KW - enantiomer separation KW - β-cyclodextrin SP - 1080 EP - 1090 JF - Chirality JO - Chirality VL - 32 IS - 8 N2 - Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/32383525/Novel_chiral_stationary_phases_based_on_3,5-dimethyl_phenylcarbamoylated_β-cyclodextrin_combining_cinchona_alkaloid_moiety L2 - https://doi.org/10.1002/chir.23237 DB - PRIME DP - Unbound Medicine ER -
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