A HILIC stationary phase fuctionalized with glutathione by thiol-ene chemistry on monodisperse-porous polymer microparticles

Yıl 2020, Cilt: 48 Sayı: 1, 21 - 31, 17.04.2020

Cigdem Kip

https://doi.org/10.15671/hjbc.567057

Öz

Monodisperse-porous
microparticles functionalized a with a zwitterionic ligand were synthesized as
a new stationary phase for hydrophilic interaction chromatography.
Monodisperse-porous poly(3-trimethoxysilylpropyl methacrylate-co-ethylene
dimethacrylate), poly(TMSPM-co-EDMA) microspheres (6 μm in size) were obtained
with different seed latex/monomer ratios and diluent compositions by multistage
microsuspension copolymerization. The zwitterionic chromatographic ligand
containing thiol moiety (i.e. glutathione) were covalently attached onto the
TMSPM attached-poly(TMSPM-co-EDMA) microparticles. The selected starting
material allowed the direct attachment of zwitterionic ligand onto the support material using thiol-ene chemistry.
The derivatized microparticles were slurry packed into the microbore columns
with 2 mm i.d. and used as stationary phase for the separation of nucleosides
in hydrophilic interaction chromatography with the plate numbers up to 54.000
plates/m. The results showed the usability 
of  tailored poly (TMSPM-co-EDMA)
microparticles as a stationary phase and thiol-ene chemistry in the manufacture
of a chromatographic stationary phase with high efficiency in hydrophilic liquid
chromatography applications.

Anahtar Kelimeler

Thiol-ene chemistry, Monodisperse-porous microparticles, Hydrophilic interaction chromatography, nucleosides

Destekleyen Kurum

Hacettepe University Scientific Research Projects Coordination Unit

Proje Numarası

FHD-2016-8480

Teşekkür

This research is supported by Hacettepe University Scientific Research Projects Coordination Unit under contract numbered as FHD-2016-8480. The author also thank Prof. Dr. Ali TUNCEL for his valuable help to use his own laboratory facilities.

Kaynakça

• Referans1. A.J. Alpert, Hydrophilic-Interaction chromatography for the separation of peptides, nucleic-Acids and other polar compounds, J. Chromatogr., 499 (1990) 177-196.
• Referans2. T. Ikegami, K. Tomomatsu, H. Takubo, K. Horie, N. Tanaka, Separation efficiencies in hydrophilic interaction chromatography, J. Chromatogr. A, 1184 (2008) 474-503.
• Referans3. Y. Guo, S. Gaiki, Retention behavior of small polar compounds on polar stationary phases in hydrophilic interaction chromatography, J. Chromatogr. A, 1074 (2005) 71–80
• Referans4. A.R. Oyler, B.L. Armstrong, J.Y. Cha, M.X. Zhou, Q. Yang, R.I. Robinson, R. Dunphy, D.J. Burinsky, Hydrophilic-Interaction Chromatography on Amino-Silica Phases Complements Reversed-Phase High Performance Liquid Chromatography and Capillary Electrophoresis for Peptide Analysis, J. Chromatogr. A., 724 (1996) 378–383.
• Referans5. T.J. Yoshida, Peptide separation by Hydrophilic-Interaction Chromatography: a review, Biochem Biophys Meth., 60 (2004) 265–280.
• Referans6. Z.G. Hao, C. Lu, B.M. Xiao, N.D. Wenig, B. Parker, M. Knapp, C. Ho, Separation of amino acids, peptides and corresponding Amadori compounds on a silica column at elevated temperature, J. Chromatogr. A., 1147 (2007) 165–171.
• Referans7. T. Ikegami, K. Tomomatsu, H. Takubo, K. Horie, N. Tanaka, Separation efficiencies in hydrophilic interaction chromatography, J. Chromatogr. A., 1184 (2008) 474-503.
• Referans8. S. Cubbon, T. Bradbury, J. Wilson, J. Thomas-Oates, Hydrophilic interaction chromatography for mass spectrometric metabonomic studies of urine, Anal Chem., 79 (2007) 8911–8918.
• Referans9. B. Buszewski, S. Noga, Hydrophilic interaction liquid chromatography (HILIC)—a powerful separation technique, Anal. Bioanal. Chem., 402 (2012) 231–247.
• Referans10. B. Alberts, A. Johnson, J. Lewis, M. Raff, K. Roberts, P. Walter, Molecular biology of the cell, New York: Garland Science, 2002.
• Referans11. N. Kochanowski, F. Blanchard, R. Cacan, F. Chirat, E. Guedon, A. Marc, J.L. Goergen, Intracellular nucleotide and nucleotide sugar contents of cultured CHO cells determined by a fast, sensitive, and high-resolution ion-pair RP-HPLC, Anal. Biochem., 348 (2006) 243–251.
• Referans12. P. Yeung, L. Ding, W.L. Casley, HPLC assay with UV detection for determination of RBC purine nucleotide concentrations and application for biomarker study in vivo, J. Pharm. Biomed. Anal., 47 (2008) 377–382.
• Referans13. X. Lv , W. Tan, Y. Chen, Y. Chen, M. Ma, B. Chen, S. Yao, Facile “one-pot” synthesis of poly(methacrylic acid)-based hybridmonolith via thiol-ene click reaction for hydrophilic interactionchromatography, J. Chromatogr. A., 1454 (2016) 49-57.
• Referans14. J. Zeng, S. Liu, M. Wang, S. Yao, Y. Chen, The synthesis of weak acidic type hybrid monolith via thiol-ene click chemistry and its application in hydrophilic interaction chromatography, Electrophoresis, 38 (2017) 1325–1333
• Referans15. J. Bai, Z. Liu, H. Wang, X. You, J. Ou, Y. Shen, M. Ye, Preparation and characterization of hydrophilic hybrid monoliths viathiol-ene click polymerization and their applications inchromatographic analysis and glycopeptides enrichment, J. Chromatogr. A., 1498 (2017) 37-45.
• Referans16. A. Shen, Z. Guo, L. Yu, L. Caoa, X. Liang, A novel zwitterionic HILIC stationary phase based on ‘‘thiol-ene’’ click chemistry between cysteine and vinyl silica, Chem. Commun., 47 (2011) 4550-4552.
• Referans17. W. Shao, J. Liu, Y. Liang, K. Yang, Y. Min, X. Zhang, Z. Liang, L. Zhang, Y. Zhang, "Thiol-ene" grafting of silica particles with three-dimensional branched copolymer for HILIC/cation-exchange chromatographic separation and N-glycopeptide enrichment, Anal. Bioanal. Chem., 410 (2018) 1019-1027.
• Referans18. A. Shen, Z. Guo, X. Cai, X. Xue, X. Liang, Preparation and chromatographic evaluation of a cysteine-bonded zwitterionic hydrophilic interaction liquid chromatography stationary phase, J Chromatogr A., 1228 (2012) 175-182.
• Referans19. C.E. Hoyle, C. Bowman, Thiol-ene click chemistry, Angew Chem. Int. Ed., 49 (2010) 1540–1573.
• Referans20. C.J. Huang, L.C. Wang, C.Y. Liu, A.S. Chiang, Y.C. Chang, Natural zwitterionic organosulfurs as surface ligands for antifouling and responsive properties, Biointerphases, 9 (2014) 029010.
• Referans21. Z. Lin, X. Tan, R. Yu, J. Lin, X. Yin, L. Zhang, H. Yang, One-pot preparation of glutathione–silica hybrid monolith formixed-mode capillary liquid chromatography based on “thiol-ene”click chemistry, J Chromatogr. A., 1355 (2014) 228-237.
• Referans22. A. Shen, X. Li, X. Dong, J. Wei, Z. Guo, X. Liang, Glutathione-based zwitterionic stationary phase for hydrophilicinteraction/cation-exchange mixed-mode chromatography, J Chromatogr. A., 1314 (2013) 63-69.
• Referans23. L. Qiao , A. Dou, X. Shi, H. Li, Y. Shan, X. Lu, G. Xu, Development and evaluation of new imidazolium-based zwitterionic stationary phases for hydrophilic interaction chromatography, J Chromatogr. A., 1286 (2013) 137-45.
• Referans24. X.T. Peng, T. Liu, S.X. Ji, Y.Q. Feng, Preparation of a novel carboxyl stationary phase by “thiol-ene” click chemistry for hydrophilic interaction chromatography, J Sep. Sci., 16 (2013) 2571-2577.
• Referans25. X. Ren, K. Zhang, D. Gao, Q. Fu, J. Zeng, D. Zhou, L. Wang, Z. Xia, Mixed-mode liquid chromatography with a stationary phase co-functionalized with ionic liquid embedded C18 and an aryl sulfonate group, J Chromatogr. A., 1564 (2018) 137-144.
• Referans26. D. Yang, D. P. Yu, X.F. Dong, A.J. Shen, G.W. Jin, Z.M. Guo, J.Y. Yan, M.Y. Liu, X.M. Liang, Chemically Bonded Polyacrylamide via Thiol-Ene Click Chemistry as Separation Materials for Hydrophilic Interaction Liquid Chromatography, Chinese J. Anal. Chem., 43 (2015) 1439-1444.
• Referans27. G. Günal, Ç. Kip, S.E. Öğüt, D.D. Usta, E. Şenlik, G. Kibar, A. Tuncel, Human genomic DNA isolation from whole blood using a simple microfluidic system with silica- and polymer-based stationary phases, Mater. Sci. Eng. C Mater. Biol. Appl., 74 (2017) 10-20.