Skip to main content

Advertisement

SpringerLink
Log in

Preparation and Enantiomeric Separation of l-Pro-l-Phe-l-Val-l-Leu Peptide Stationary Phases

  • Original
  • Published:
Chromatographia Aims and scope Submit manuscript

Abstract

This study presents the development of three new chiral stationary phases. Three new peptide chiral stationary phases with a main chain of l-proline, l-phenylalanine, l-valine and l-leucine and different terminals of l-citrulline, l-lysine and l-tryptophan immobilized on 3-aminopropyltrimethoxysilane modified silica gel were prepared; furthermore, successful analyses and characterizations were conducted using Fourier transform infrared spectra, elemental analysis, and thermogravimetric analysis. After this, the enantioselective performance of the three peptide stationary phases columns was evaluated. The evaluation used nine racemic compounds under normal-phase high-performance liquid chromatography mode. Optimized enantiomeric separation conditions were established. Under these conditions, the resolutions of flurbiprofen, naproxen, benzoin, 1,1ʹ-bi-2-naphthol and ketoprofen on the CSP-1 column were 1.61, 2.0, 0.62, 0.52 and 1.20, respectively. In addition, the reproducibility of the CSP-1 column was also investigated. The results of the investigation illustrated that the stationary phases have good reproducibility (RSD = 0.12%, n = 5).

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.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

Data availability

The data underlying this article are available in the article and in its supplementary material.

References

  1. Qi L, Qiao J (2022) Progress of chiral ligand-exchange capillary electrophoresis for enantioseparation. J Chromatogr A 1679:63381. https://doi.org/10.1016/j.chroma.2022.463381

    Article  CAS  Google Scholar 

  2. Cheng QS, Ma Q, Pei HB, Liang H, Zhang XJ, Jin XN, Liu NJ, Guo RB, Mo ZL (2023) Chiral metal-organic frameworks materials for racemate resolution. Coordin Chem Rev 484: 215120. https://doi.org/10.1016/j.ccr.2023.215120

  3. Brooks W, Guida W, Daniel K (2011) The significance of chirality in drug design and development. Curr Top Med Chem 760: 11. https://doi.org/10.2174/156802611795165098

  4. Blaser HU (2013) Chirality and its implications for the pharmaceutical industry. Rend Lincei 24:213–216. https://doi.org/10.1007/s12210-012-0220-2

    Article  Google Scholar 

  5. Zhu QJ, Cai ZW, Zhou PL, Sun XX, Xu J (2023) Recent progress of membrane technology for chiral separation: a comprehensive review. Sep Purif Technol 309: 123077. https://doi.org/10.1016/j.seppur.2022.123077

  6. Mane S (2016) Racemic drug resolution: a comprehensive guide. Anal Methods 8:567–7586. https://doi.org/10.1039/c6ay02015a

    Article  Google Scholar 

  7. Gao H, Fu LL, Cai ML, Chen W, Bai ZW (2021) Preparation of 6-amino-6-deoxy cellulose and its derivatives used as chiral separation materials. Carbohydr Polym 259: 117756. https://doi.org/10.1016/j.carbpol.2021.117756

  8. Peluso P, Mamane V, Dallocchio R, DessìA CS (2020) Noncovalent interactions in high-performance liquid chromatography enantioseparations on polysaccharide-based chiral selectors. J Chromatogr A 1623:46120. https://doi.org/10.1016/j.chroma.2020.461202

    Article  CAS  Google Scholar 

  9. Chankvetadze B (2020) Recent trends in preparation, investigation and application of polysaccharide-based chiral stationary phases for separation of enantiomers in high-performance liquid chromatograph. Trends Anal Chem 122: 115709. https://doi.org/10.1016/j.trac.2019.115709

  10. Chankvetadze B (2012) Recent developments on polysaccharide-based chiral stationary phases for liquid-phase separation of enantiomers. J Chromatogr A 1269:26–51. https://doi.org/10.1016/j.chroma.2012.10.033

    Article  CAS  PubMed  Google Scholar 

  11. Tsui HW, Ye PW, Huang X (2020) Effect of solvents on the chiral recognition mechanisms of immobilized cellulose-based chiral stationary phase. J chromatogr A 1637: 461796. https://doi.org/10.1016/j.chroma.2020.461796

  12. Shen J, Okamoto Y (2016) Efficient separation of enantiomers using stereoregular chiral polymers. Chem Rev 116:1094–1138. https://doi.org/10.1021/acs.chemrev.5b00317

    Article  CAS  PubMed  Google Scholar 

  13. Ferraro JM, Umstead WJ (2023) Chiral separation of cannabichromene, cannabicyclol and their acidic analogs on polysaccharide chiral stationary phases. Molecules 28:1164. https://doi.org/10.3390/molecules28031164

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Zeng QL, Wen Q, Xiang Y, Zhang L (2018) Chiral stationary phases. J Chromatogr A 1571:240–244. https://doi.org/10.1016/j.chroma.2018.08.010

    Article  CAS  PubMed  Google Scholar 

  15. Kažoka H, Turovska B, Upmanis T, Veinberg G (2022) Enantioseparation of 4C-substituted pyrrolidin-2-one derivatives on polysaccharide and macrocyclic glycopeptide chiral stationary phases. Chromatographia 85:489–495. https://doi.org/10.1007/s10337-022-04145-z

    Article  CAS  Google Scholar 

  16. Syame KR, Caroline W (2019) Characterization of three macrocyclic glycopeptide stationary phases in supercritical fluid chromatography. J Chromatogr A 160:4460–4485. https://doi.org/10.1016/j.chroma.2019.460485

    Article  CAS  Google Scholar 

  17. Xu SJ, Wang YY, Tang YX, Ji YB (2018) A protein-based mixed selector chiral monolithic stationary phase in capillary electrochromatography. New J Chem 42:13520–13528. https://doi.org/10.1039/c8nj02309c

    Article  CAS  Google Scholar 

  18. Tang S, Wang W, Hou HP, Liu YQ, Liu K, Geng N, Sun LQ, Luo AQ (2022) A β-cyclodextrin covalent organic framework used as a chiral stationary phase for chiral separation in gas chromatography. Chin Chem Let 33:898–902. https://doi.org/10.1016/j.cclet.2021.06.089

    Article  CAS  Google Scholar 

  19. Ohnishi A, Shibata T, Imase T, Shinkura S, Nagai K (2021) Achiral molecular recognition of substituted aniline position isomers by crown ether type chiral stationary phase. Molecules 493:26. https://doi.org/10.3390/molecules26020493

    Article  CAS  Google Scholar 

  20. Sung JY, Jin M, Lee SM, An SY, Jin JS (2021) Unusual enantiomeric separation due to residual amines in chiral crown ether stationary phase linked by long alkyl chain. Talanta 235: 122739. https://doi.org/10.1016/j.talanta.2021.122739

  21. Chen H, Gu ZG, Zhang J (2012) Surface chiroselective assembly of enantiopure crystalline porous films containing bichiral building blocks. Chem Sci 12: 12346–12352. https://doi.org/10.1039/d1sc03089b

  22. Slater B, Hill M, Ladewig B (2021) Solvent-induced enantioselectivity reversal in a chiral metal organic framework. J Sep Sc 44:3319–3323. https://doi.org/10.1002/jssc.202100322

    Article  CAS  Google Scholar 

  23. Ismail O, Pasti L, Ciogli A, Villani C, Kocergin J, Anderson S, Gasparrini FA, Cavazzini A, Catani M (2016) Pirkle-type chiral stationary phase on core-shell and fully porous particles: are superficially porous particles always the better choice toward ultrafast high-performance enantioseparations. J Chromatogr A 1466:96–104. https://doi.org/10.1016/j.chroma.2016.09.001

    Article  CAS  PubMed  Google Scholar 

  24. Huang M, Chen H, Li TY (2006) Improvement of proline chiral stationary phases by varying peptide length and linker. J Chromatogr A 1113:109–115. https://doi.org/10.1016/j.chroma.2006.01.128

    Article  CAS  PubMed  Google Scholar 

  25. Huang JM, Zhang P, Chen H, Li TY (2005) Preparation and evaluation of proline-based chiral columns. Anal Chem 77:3301–3308. https://doi.org/10.1021/ac050050s

    Article  CAS  PubMed  Google Scholar 

  26. Buszewski B, Skoczylas M (2019) Multi-parametric characterization of amino acid-and peptide-silica stationary phases. Chromatographia 82:153–166. https://doi.org/10.1007/s10337-018-3569-2

    Article  CAS  Google Scholar 

  27. Ma ZY, Shang PP, Liu DL, Nie YY, Liu YL, Guo XY, Wei BB, Bai LG, Qiao XQ (2023) Preparation and chromatographic performance of chiral peptide-based stationary phases for enantiomeric separation. Chirality 1–9. https://doi.org/10.1002/chir.23564

  28. Li Y, Jiang DJ, Huang DY, Huang MX, Lia LJ (2015) Preparation and characterization of tripeptide chiral stationary phases with varying amino acid sequences and terminal groups. Anal Methods 7:3772–3778. https://doi.org/10.1039/c5ay00691k

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by grants from Hebei Natural Science Foundation (nos. H2017201075, B2020201056).

Author information

Authors and Affiliations

  1. Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, 071002, China

    Xinyuan Guo, Panpan Shang, Benben Wei, Wenrong Du, Yong Lan, Ligai Bai, Xiaoqiang Qiao & Zhengyue Ma

Authors
  1. Xinyuan Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Panpan Shang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Benben Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wenrong Du
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yong Lan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ligai Bai
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Xiaoqiang Qiao
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Zhengyue Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by Xinyuan Guo and Panpan Shang. The first draft of the manuscript was written by Xinyuan Guo. Research program planning and writing—review and editing were performed by Benben Wei and Wenrong Du. Conceptualization, writing—review and editing, supervision, project administration and funding acquisition were performed by Wenrong Du and Yong Lan. Zhengyue Ma revised the whole manuscript and finished the final draft. Xiaoqiang Qiao and Ligai Bai put forward some useful suggestions for the revision and improvement of the manuscript. All authors read and approved the final manuscript.

Corresponding author

Correspondence to Zhengyue Ma.

Ethics declarations

Conflict of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 634 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Guo, X., Shang, P., Wei, B. et al. Preparation and Enantiomeric Separation of l-Pro-l-Phe-l-Val-l-Leu Peptide Stationary Phases. Chromatographia 86, 541–551 (2023). https://doi.org/10.1007/s10337-023-04267-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10337-023-04267-y

Keywords

Search

Navigation