Separation of N-derivatized di- and tri-peptide stereoisomers by micro-liquid chromatography using a quinidine-based monolithic column - Analysis of l-carnosine in dietary supplements. - 2015
Separation of N-derivatized di- and tri-peptide stereoisomers by micro-liquid chromatography using a quinidine-based monolithic column - Analysis of l-carnosine in dietary supplements.
Carnosine; Dietary supplements; Enantioseparation; Quinidine-based monolithic column; Small peptides
Résumé :
[en] In the present study, a new analytical methodology was developed enabling the enantiomeric determination of N-derivatized di- and tri-peptides in dietary supplements using chiral micro-LC on a monolithic column consisting of poly(O-9-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine-co-2-hydroxy ethyl methacrylate-co-ethylene dimethacrylate) (poly(MQD-co-HEMA-co-EDMA)). After optimization of the mobile phase conditions, a baseline resolution of the stereoisomers of 24 out of 53 N-derivatized di- and tri-peptides was obtained. 3,5-Dinitrobenzoyl- and 3,5-dichlorobenzoyl-peptide stereoisomers were separated with exceptionally high selectivity and resolution. The monolithic column was then applied to the quantitative analysis of l-carnosine and its enantiomeric impurity in three different commercial dietary supplements. Method validation demonstrated satisfactory results in terms of linearity, precision, selectivity, accuracy and limits of detection and quantification. The determined amounts of l-carnosine in commercial formulations were in agreement with the labeled content for all analyzed samples, and the enantiomeric impurity was found to be below the limit of detection (LOD), showing the potential of the poly(MQD-co-HEMA-co-EDMA) monolithic column as a reliable tool for the quality control of l-carnosine in dietary supplements by micro-LC.
Centre/Unité de recherche :
Centre Interfacultaire de Recherche du Médicament - CIRM
Disciplines :
Pharmacie, pharmacologie & toxicologie
Auteur, co-auteur :
Wang, Qiqin
Sanchez-Lopez, Elena
Han, Hai
Wu, Huihui
Zhu, Peijie
Crommen, Jacques ; Université de Liège > Département de pharmacie > Analyse des Médicaments
Marina, Maria Luisa
Jiang, Zhengjin
Langue du document :
Anglais
Titre :
Separation of N-derivatized di- and tri-peptide stereoisomers by micro-liquid chromatography using a quinidine-based monolithic column - Analysis of l-carnosine in dietary supplements.
Date de publication/diffusion :
2015
Titre du périodique :
Journal of Chromatography. A
ISSN :
0021-9673
eISSN :
1873-3778
Maison d'édition :
Elsevier, Amsterdam, Pays-Bas
Peer reviewed :
Peer reviewed vérifié par ORBi
Commentaire :
Copyright (c) 2015 Elsevier B.V. All rights reserved.
Liao J., Lin I., Huang K., Kuo P., Wu S., Wu T. Carnosine ameliorates lens protein turbidity formations by inhibiting calpain proteolysis and ultraviolet c-induced degradation. J. Agric. Food Chem. 2014, 62:5932-5938.
Lanza V., Bellia F., D'Agata R., Grasso G., Rizzarelli E., Vecchio G. New glycoside derivatives of carnosine and analogs resistant to carnosinase hydrolysis: synthesis and characterization of their copper (II) complexes. J. Inorg. Biochem. 2011, 105:181-188.
Boldyrev A.A., Aldini G., Derave W. Physiology and pathophysiology of carnosine. Physiol. Rev. 2013, 93:1803-1845.
Kohen R., Yamamoto Y., Cundy K.C., Ames B.N. Antioxidant activity of carnosine, homocarnosine, and anserine present in muscle and brain. Proc. Natl. Acad. Sci. U. S. A. 1988, 85:3175-3179.
Grasso G.I., Bellia F., Arena G., Vecchio G., Rizzarelli E. Noncovalent interaction-driven stereoselectivity of copper (II) complexes with cyclodextrin derivatives of l- and d-carnosine. Inorg. Chem. 2011, 50:4917-4924.
Su D., Bi K., Zhou C., Song Y., Wei B., Geng L., Liu W., Chen X. Enantioselective separation and determination of carnosine in rat plasma by fluorescence LC for stereoselective pharmacokinetic studies. Chromatographia 2010, 71:603-608.
Sungthong B., Iványi R., Bunz S.C., Neusüß C., Scriba G.K.E. CE-MS characterization of negatively charged α-, β- and γ-CD derivatives and their application to the separation of dipeptide and tripeptide enantiomers by CE. Electrophoresis 2010, 31:1498-1505.
Ali I., Al-Othman Z.A., Al-Warthan A., Asnin L., Chudinov A. Advances in chiral separations of small peptides by capillary electrophoresis and chromatography. J. Sep. Sci. 2014, 37:2447-2466.
Ludewig R., Nietzsche S., Scriba G.K.E. A weak cation-exchange monolith as stationary phase for the separation of peptide diastereomers by CEC. J. Sep. Sci. 2011, 34:64-69.
Scriba G.K.E. Recent developments in peptide stereoisomer separations by capillary electromigration techniques. Electrophoresis 2009, 30:S222-S228.
Kašička V. Recent developments in capillary and microchip electroseparations of peptides (2011-2013). Electrophoresis 2014, 35:69-95.
Czerwenka C., Maier N.M., Lindner W. Liquid chromatographic-mass spectrometric separation of oligoalanine peptide stereoisomers: influence of absolute configuration on enantioselectivity and two-dimensional separation of diastereomers and enantiomers. J. Chromatogr. A 2004, 1038:85-95.
Czerwenka C., Lämmerhofer M., Lindner W. Micro-HPLC and standard-size HPLC for the separation of peptide stereoisomers employing an ion-exchange principle. J. Pharm. Biomed. Anal. 2003, 30:1789-1800.
Conrad U., Chankvetadze B., Scriba G.K.E. High performance liquid chromatographic separation of dipeptide and tripeptide enantiomers using a chiral crown ether stationary phase. J. Sep. Sci. 2005, 28:2275-2281.
Esquivel B., Nicholson L., Peerey L. Enantiomeric resolution of underivatized small peptides by HPLC with a chiral crown ether stationary phase. J. High Resolut. Chromatogr. 1991, 14:816-823.
Hilton M., Armstrong D.W. Evaluation of the enantiomeric separation of dipeptides using a chiral crown ether LC column. J. Liq. Chromatogr. 1991, 14:3673-3683.
Schmid M.G., Hölbling M., Schnedlitz N., Gübitz G. Enantioseparation of dipeptides and tripeptides by micro-HPLC comparing teicoplanin and teicoplanin aglycone as chiral selectors. J. Biochem. Biophys. Methods 2004, 61:1-10.
Berthod A., Liu Y., Bagwill C., Armstrong D.W. Facile liquid chromatographic enantioresolution of native amino acids and peptides using a teicoplanin chiral stationary phase. J. Chromatogr. A 1996, 731:123-137.
Chen S. The HPLC resolution of N-2,4-dinitrophenylated amino acids and peptides stereoisomers on naphthylethylcarbamate-β-cyclodextrin bonded phase using the acetonitrile-based mobile phase: evidence for the chiral recognition pattern. Amino Acids 2004, 27:277-284.
Chen S. The facile HPLC enantioresolution of amino acids, peptides on naphthylethylcarbamate-β-cyclodextrin bonded phases using the acetonitrile-based mobile phase after their pre-column derivatization with phenyl isothiocyanate: factors that affect the resolution. Amino Acids 2004, 26:291-298.
Schiesel S., Lämmerhofer M., Leitner A., Lindner W. Quantitative high-performance liquid chromatography-tandem mass spectrometry impurity profiling methods for the analysis of parenteral infusion solutions for amino acid supplementation containing l-alanyl-l-glutamine. J. Chromatogr. A 2012, 1259:111-120.
Wernisch S., Trapp O., Lindner W. Application of cinchona-sulfonate-based chiral zwitterionic ion exchangers for the separation of proline-containing dipeptide rotamers and determination of on-column isomerization parameters from dynamic elution profiles. Anal. Chim. Acta 2013, 795:88-98.
Wernisch S., Lindner W. Versatility of cinchona-based zwitterionic chiral stationary phases: enantiomer and diastereomer separations of non-protected oligopeptides utilizing a multi-modal chiral recognition mechanism. J. Chromatogr. A 2012, 1269:297-307.
Mucha A., Lämmerhofer M., Lindner W., Pawelczak M., Kafarski P. Individual stereoisomers of phosphinic dipeptide inhibitor of leucine aminopeptidase. Bioorg. Med. Chem. Lett. 2008, 18:1550-1554.
Czerwenka C., Polásková P., Lindner W. Peptide enantiomer separations: influence of sequential isomerism and the introduction of achiral glycine moieties on chiral recognition. J. Chromatogr. A 2005, 1093:81-88.
Preinerstorfer B., Lubda D., Mucha A., Kafarski P., Lindner W., Lämmerhofer M. Stereoselective separations of chiral phosphinic acid pseudodipeptides by CEC using silica monoliths modified with an anion-exchange-type chiral selector. Electrophoresis 2006, 27:4312-4320.
Bobbitt J.M., Li L., Carlton D.D., Yasin M., Bhawal S., Foss F.W., Wernisch S., Pell R., Lindner W., Schug K.A. Diastereoselective discrimination of lysine-alanine-alanine peptides by zwitterionic cinchona alkaloid-based chiral selectors using electrospray ionization mass spectrometry. J. Chromatogr. A 2012, 1269:308-315.
Czerwenka C., Lindner W. Enantiomer discrimination of peptides by tandem mass spectrometry: influence of the peptide sequence on chiral recognition. Rapid Commun. Mass Spectrom. 2004, 18:2713-2718.
Czerwenka C., Lämmerhofer M., Lindner W. Electrolyte and additive effects on enantiomer separation of peptides by nonaqueous ion-pair capillary electrophoresis using tert.-butylcarbamoylquinine as chiral counterion. Electrophoresis 2002, 23:1887-1899.
Wang Q., Feng J., Han H., Zhu P., Wu H., Marina M.L., Crommen J., Jiang Z. Enantioseparation of N-derivatized amino acids by micro-liquid chromatography using carbamoylated quinidine functionalized monolithic stationary phase. J. Chromatogr. A 2014, 1363:207-215.
Jiang Z., Smith N.W., Ferguson P.D., Taylor M.R. Hydrophilic interaction chromatography using methacrylate-based monolithic capillary column for the separation of polar analytes. Anal. Chem. 2007, 79:1243-1250.
Minakuchi H., Nakanishi K., Soga N., Ishizuka N., Tanaka N. Octadecylsilylated porous silica rods as separation media for reversed-phase liquid chromatography. Anal. Chem. 1996, 68:3498-3501.
Svec F. Porous polymer monoliths: amazingly wide variety of techniques enabling their preparation. J. Chromatogr. A 2010, 1217:902-924.
Lämmerhofer M., Peters E.C., Yu C., Svec F., Fréchet J.M.J. Chiral monolithic columns for enantioselective capillary electrochromatography prepared by copolymerization of a monomer with quinidine functionality. 1. Optimization of polymerization conditions, porous properties, and chemistry of the stationary phase. Anal. Chem. 2000, 72:4614-4622.
Lämmerhofer M., Svec F., Fréchet J.M.J. Chiral monolithic columns for enantioselective capillary electrochromatography prepared by copolymerization of a monomer with quinidine functionality. 2. Effect of chromatographic conditions on the chiral separations. Anal. Chem. 2000, 72:4623-4628.
Pirkle W.H., Pochapsky T.C. Chiral molecular recognition in small bimolecular systems: a spectroscopic investigation into the nature of diastereomeric complexes. J. Am. Chem. Soc. 1987, 109:5975-5982.
Wan H., Andersson P.E., Engström A., Blomberg L.G. Direct and indirect chiral separation of amino acids by capillary electrophoresis. J. Chromatogr. A 1995, 704:179-193.
Domínguez-Vega E., Crego A.L., Lomsadze K., Chankvetadze B., Marina M.L. Enantiomeric separation of FMOC-amino acids by nano-LC and CEC using a new chiral stationary phase, cellulose tris(3-chloro-4-methylphenylcarbamate). Electrophoresis 2011, 32:2700-2707.
Domínguez-Vega E., Martínez-Girón A.B., García-Ruiz C., Crego A.L., Marina M.L. Fast derivatization of the non-protein amino acid ornithine with FITC using an ultrasound probe prior to enantiomeric determination in food supplements by EKC. Electrophoresis 2009, 30:1037-1045.
Zhang Q., Guo J., Wang F., Crommen J., Jiang Z. Preparation of a β-cyclodextrin functionalized monolith via a novel and simple one-pot approach and application to enantioseparations. J. Chromatogr. A 2014, 1325:147-154.
Piette V., Lämmerhofer M., Lindner W., Crommen J. Enantiomer separation of N-protected amino acids by non-aqueous capillary electrophoresis and high-performance liquid chromatography with tert.-butyl carbamoylated quinine in either the background electrolyte or the stationary phase. J. Chromatogr. A 2003, 987:421-427.
Czerwenka C., Lämmerhofer M., Maier N.M., Rissanen K., Lindner W. Direct high-performance liquid chromatographic separation of peptide enantiomers: study on chiral recognition by systematic evaluation of the influence of structural features of the chiral selectors on enantioselectivity. Anal. Chem. 2002, 74:5658-5666.
Czerwenka C., Zhang M., Kählig H., Maier N.M., Lipkowitz K.B., Lindner W. Chiral recognition of peptide enantiomers by cinchona alkaloid derived chiral selectors: mechanistic investigations by liquid chromatography, NMR spectroscopy, and molecular modeling. J. Org. Chem. 2003, 68:8315-8327.
Czerwenka C., Lämmerhofer M., Lindner W. Structure-enantioselectivity relationships for the study of chiral recognition in peptide enantiomer separation on cinchona alkaloid-based chiral stationary phases by HPLC: influence of the N-terminal protecting group. J. Sep. Sci. 2003, 26:1499-1508.
Czerwenka C., Maier N.M., Lindner W. Enantiomer discrimination by mass spectrometry: noncovalent interactions of an N-derivatized dipeptide with various cinchona alkaloid derivatives and comparison with enantioselective liquid-phase separations. Anal. Bioanal. Chem. 2004, 379:1039-1044.
Husson E., Humeau C., Harscoat C., Framboisier X., Paris C., Dubreucq E., Marc I., Chevalot I. Enzymatic acylation of the polar dipeptide, carnosine: reaction performances in organic and aqueous media. Process Biochem. 2011, 46:945-952.
Jámbor A., Molnár-Perl I. Quantitation of amino acids in plasma by high performance liquid chromatography: simultaneous deproteinization and derivatization with 9-fluorenylmethyloxycarbonyl chloride. J. Chromatogr. A 2009, 1216:6218-6223.