Skip to main content
SpringerLink
Log in

Preparation and Application of Partially Substituted Phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-Appended Silica Particles as Chiral Stationary Phase for Multi-mode HPLC

  • Short Communication
  • Published:
Chromatographia Aims and scope Submit manuscript

Abstract

A new type of partially substituted cyclodextrin-bonded silica particles, phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-appended silica (P-CD-HPS), has been successfully prepared and used as chiral stationary phase (CSP) in high-performance liquid chromatography (HPLC) under normal-phase, reversed-phase, and polar organic mobile-phase conditions. The P-CD-HPS was characterized by elemental analysis and Fourier transform infrared spectroscopic (FTIR) analysis. The chromatographic performance of the new-phase P-CD-HPS has been evaluated in HPLC under multi-mode conditions via separating positional isomers of some disubstituted benzenes and enantiomers of some chiral drug compounds. The separation results show that P-CD-HPS exhibited excellent selectivity for separating the positional isomers of nitrophenol and nitraniline and the enantiomers of some chiral drug compounds. The hydroxyl residues of partially substituted β-cyclodextrin and chiral spacer linking to secondary hydroxyl site of the β-cyclodextrin in the P-CD-HPS not only have important contributions to chiral recognitions and separations, but also allow the P-CD-HPS to be used under multi-mode mobile-phase conditions in HPLC.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Abbreviations

P-CD-HPS:

Phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-appended silica

CSP:

Chiral stationary phase

FTIR:

Fourier transform infrared spectroscopic analysis

References

  1. Yang B, Zhou J, Wang Y, Tang J (2017) Enantioseparation of isoxazolines with functionalized perphenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC. Electrophoresis 38:1939–1947

    Article  CAS  Google Scholar 

  2. Shen J, Okamoto Y (2016) Efficient separation of enantiomers using stereoregular chiral polymers. Chem Rev 116:1094–1138

    Article  CAS  Google Scholar 

  3. Wang Y, Zhang S, Breitbach ZS, Petersen H, Ellegaard P, Armstrong DW (2016) Enantioseparation of citalopram analogues with sulfated β-cyclodextrin by capillary electrophoresis. Electrophoresis 37:841–848

    Article  CAS  Google Scholar 

  4. Gumustas M, Ozkan SA, Chankvetadze B (2018) Analytical and preparative scale separation of enantiomers of chiral drugs by chromatography and related methods. Curr Med Chem 25:4152–4188

    Article  CAS  Google Scholar 

  5. Xu C, Ng SC, Chan HSO (2008) Self-assembly of perfunctionalized β-cyclodextrins on a quartz crystal microbalance for real-time chiral recognition. Langmuir 24:9118–9124

    Article  CAS  Google Scholar 

  6. Lin C, Fan J, Liu W, Chen X, Ruan L, Zhang W (2018) A new single-urea-bound 3,5-dimethylphenylcarbamoylated β-cyclodextrin chiral stationary phase and its enhanced separation performance in normal-phase liquid chromatography. Electrophoresis 39:348–355

    Article  CAS  Google Scholar 

  7. Bai W, Ching B, Ng SC (2003) Monochloro-substituted phenyl carbamoylated β-cyclodextrins as π-acid chiral stationary phases for high-performance liquid chromatography. Chromatographia 58:43–46

    CAS  Google Scholar 

  8. AhmedK Si, Tazerouti F, Badjah-Hadj-Ahmed AY, Meklati BY (2007) Preparation and chromatographic properties of a multimodal chiral stationary phase based on phenyl-carbamate-propyl-β-CD for HPLC. J Sep Sci 30:2025–2036

    Article  Google Scholar 

  9. Zhang Z, Wu M, Wu R, Dong J, Ou J, Zou H (2011) Preparation of perphenylcarbamoylated β-cyclodextrin-silica hybrid monolithic column with “one-pot” approach for enantioseparation by capillary liquid chromatography. Anal Chem 83:3616–3622

    Article  CAS  Google Scholar 

  10. Xiao Y, Ng SC, Tan TTY, Wang Y (2012) Recent development of cyclodextrin chiral stationary phases and their applications in chromatography. J Chromatogr A 1269:52–68

    Article  CAS  Google Scholar 

  11. Muderawan IW, Ong TT, Ng SC (2006) Urea bonded cyclodextrin derivatives onto silica for chiral HPLC. J Sep Sci 29:1849–1871

    Article  CAS  Google Scholar 

  12. Poon YF, Muderawan IW, Ng SC (2006) Synthesis and application of mono-2A-azido-2A-deoxyperphenylcarbamoylated β-cyclodextrin and mono-2A-azido-2A-deoxyperacetylated β-cyclodextrin as chiral stationary phases for high-performance liquid chromatography. J Chromatogr A 1101:185–197

    Article  CAS  Google Scholar 

  13. Ma M, Wei Q, Meng M, Yin J, Du L, Zhu X, Min M, Zhou X, Yin X, Gong Y (2017) Application of partially substituted 3,5-dimethylphenylcarbamate-(3-(2-o-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-appended silica particles as chiral stationary phase for multi-mode high-performance liquid chromatography. J Chromatogr Sci 55:839–845

    Article  CAS  Google Scholar 

  14. Pang L, Zhou J, Tang J, Ng SC, Tang W (2014) Evaluation of perphenylcarbamated cyclodextrin clicked chiral stationary phase for enantioseparations in reversed phase high performance liquid chromatography. J Chromatogr A 1363:119–127

    Article  CAS  Google Scholar 

  15. Lin Y, Zhou J, Tang J, Tang W (2015) Cyclodextrin clicked chiral stationary phases with functionalities-tuned enantioseparations in high performance liquid chromatography. J Chromatogr A 1406:342–346

    Article  CAS  Google Scholar 

  16. Tang J, Pang L, Zhou J, Zhang S, Tang W (2016) Per(3-chloro-4-methyl) phenylcarbamate cyclodextrin clicked stationary phase for chiral separation in multiple modes high-performance liquid chromatography. Anal Chim Acta 94:96–103

    Article  Google Scholar 

  17. Gong Y, Xue G, Bradshaw JS, Lee ML, Lee HK (2001) Synthesis of crown ether-capped 3-(β-cyclodextrin)-2-hydroxypropylsilyl-appended silica particles for use as chiral stationary phases in chromatography. J Heterocyclic Chem 38:1317–1321

    Article  CAS  Google Scholar 

  18. Meng M, Ma M, Yi J, Xu L, Yin X, Gu Q, Yin J, Du L, Zhu X, Zhou X et al (2019) Preparation and evaluation of partially-substituted 3-chloro-4-methylphenylcarbamate-β-cyclodextrin bonded silica particles as chiral stationary phase for multi-mode HPLC. Sep Sci Plus 2:4–11

    Article  CAS  Google Scholar 

  19. Thamarai CSK, Yong EL, Gong Y (2010) Application of bromoacetate-substituted β-CD-bonded silica particles as chiral stationary phase for HPLC. J Sep Sci 33:74–78

    Article  Google Scholar 

  20. Da S, Feng Y, Da Y, Gong Y, Zhang Y (1999) Preparation and characterization of 3-(aza-18-crown-6) propylsilyl bonded phase for reversed-phase liquid chromatography. J Chromatogr Sci 37:137–144

    Article  CAS  Google Scholar 

  21. Armstrong DW, DeMond W (1984) Cyclodextrin bonded phases for the liquid chromatographic separation of optical, geometrical, and structural isomers. J Chromatogr Sci 22:411–415

    Article  CAS  Google Scholar 

  22. Zhou ZM, Li X, Chen XP, Fang M, Dong X (2010) Separation performance and recognition mechanism of mono(6-deoxy-Imino)-β-cyclodextrins chiral stationary bases in high-performance liquid chromatography. Talanta 82:775–784

    Article  CAS  Google Scholar 

  23. Gong Y, Lee HK (2003) Application of naphthylcarbamate-substituted β-cyclodextrin bonded silica particles as stationary phase for high-performance liquid chromatography. J Sep Sci 26:515–520

    Article  CAS  Google Scholar 

  24. Hargitai T, Okamoto Y (1993) Evaluation of 3,5-dimethylphenyl carbamoylated α-, β-, and γ-cyclodextrins as chiral stationary phases for HPLC. J Chromatogr 16:843–859

    CAS  Google Scholar 

  25. Lai X, Tang W, Ng SC (2011) Novel cyclodextrin chiral stationary phases for high performance liquid chromatography enantioseparation: effect of cyclodextrin type. J Chromatogr A 1218:5597–5601

    Article  CAS  Google Scholar 

  26. Lai X, Tang W, Ng SC (2011) Novel β-cyclodextrin chiral stationary phases with different length spacers for normal-phase high performance liquid chromatography enantioseparation. J Chromatogr A 1218:3496–3501

    Article  CAS  Google Scholar 

  27. Huang G, Ou J, Zhang X, Ji Y, Peng X, Zou H (2014) Synthesis of novel perphenylcarbamated β-cyclodextrin based chiral stationary phases via thiol-ene click chemistry. Electrophoresis 35:2752–2758

    Article  CAS  Google Scholar 

  28. Cirilli R, Simonelli A, Ferretti R, Bolasco A, Chimenti P, Secci D, Maccioni E, La Torre F (2006) Analytical and semipreparative high performance liquid chromatography enantioseparation of new substituted 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)-pyrazoles on polysaccharide-based chiral stationary phases in normal-phase, polar organic and reversed-phase conditions. J Chromatogr A 1101:198–203

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank Xuzhou Medical University for financial support of this work (Grant no. 531150).

Author information

Author notes

  1. Jingxuan Yi and Lu Xu are joint first authors.

Authors and Affiliations

  1. Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, Xuzhou Medical University, 209 Tongshan Road, Xuzhou, 221004, People’s Republic of China

    Jingxuan Yi, Lu Xu, Hui Wang, Xiaoxing Yin, Xueyan Zhou, Jiale Yin, Yinan Wang, Qunli Wei & Yinhan Gong

  2. Chiraltek Pte Ltd, 192 Westwood Crescent, Singapore, 648559, Singapore

    Jasmine Hou

Authors
  1. Jingxuan Yi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lu Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hui Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiaoxing Yin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xueyan Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jiale Yin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yinan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Jasmine Hou
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Qunli Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Yinhan Gong
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Qunli Wei or Yinhan Gong.

Ethics declarations

Conflict of interest

All authors declare that they have no conflict of interest.

Ethical standards

This article does not contain any studies with human participants or animals performed by any of the authors.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yi, J., Xu, L., Wang, H. et al. Preparation and Application of Partially Substituted Phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-Appended Silica Particles as Chiral Stationary Phase for Multi-mode HPLC. Chromatographia 83, 1021–1028 (2020). https://doi.org/10.1007/s10337-020-03908-w

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10337-020-03908-w

Keywords

Search

Navigation