Enantiomeric separation of free l - And d -amino acids in hydrolyzed protein fertilizers by capillary electrophoresis tandem mass spectrometry

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 21, 2013, Pages 5022-5030

  Sánchez Hernández, Laura ^a   Serra, Nuria Sierras ^b   Marina, María Luisa ^a   Crego, Antonio L ^a  

^a UNIVERSITY OF ALCALÁ   (Spain)

^b BIOIBERICA SA   (Spain)

Author keywords

amino acids; biostimulants; chemical hydrolysis; chiral separation; cyclodextrins; enzymatic hydrolysis; fertilizers; racemization degree

Indexed keywords

BIOSTIMULANTS; CHEMICAL HYDROLYSIS; CHIRAL SEPARATIONS; ENANTIOMERIC SEPARATION; HYDROLYZED PROTEINS; LIMITS OF DETECTION; RACEMIZATION DEGREE; TANDEM MASS SPECTROMETRY;

CAPILLARY ELECTROPHORESIS; CHIRALITY; CYCLODEXTRINS; ENANTIOMERS; ENZYMATIC HYDROLYSIS; FERTILIZERS; MASS SPECTROMETRY; POLYPEPTIDES; PROTEINS; SEPARATION; STEREOCHEMISTRY;

AMINO ACIDS;

AMINO ACID; FERTILIZER;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMISTRY; EVALUATION STUDY; HYDROLYSIS; ISOLATION AND PURIFICATION; METHODOLOGY; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

AMINO ACIDS; ELECTROPHORESIS, CAPILLARY; FERTILIZERS; HYDROLYSIS; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

EID: 84878397022     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4013345     Document Type: Article

References (40)

1. Barneix, A. J.; Causin, H. F. The central role of amino acids on nitrogen utilization and plant growth J. Plant Physiol. 1996, 149, 358-362
2. Rai, V. K. Role of amino acids in plant responses to stresses Biol. Plant. 2002, 45, 481-487
3. Kauffman, G. L., III; Kneivel, D. P.; Watschke, T. L. Effects of a biostimulant on the heat tolerance associated with photosynthetic capacity, membrane thermostability, and polyphenol production of perennial ryegrass Crop Sci. 2007, 47, 261-267
4. Kolomaznik, K.; Pecha, J.; Friebrova, V.; Janacova, D.; Vasek, V. Diffusion of biostimulators into plant tissues Heat Mass Transfer 2012, 48, 1505-1512
5. Gördes, D.; Kolukisaoglu, U.; Thurow, K. Uptake and conversion of d -amino acids in Arabidopsis thaliana Amino Acids 2011, 40, 553-563
6. Brückner, H.; Westhauser, T. Chromatographic determination of l-and d -amino acids in plants Amino Acids 2003, 24, 43-55
7. Forsum, O.; Svennerstam, H.; Ganeteg, U.; Näsholm, T. Capacities and constraints of amino acid utilization in Arabidopsis New Phytol. 2008, 179, 1058-1069
8. Vranova, V.; Zahradnickova, H.; Janous, D.; Skene, K. R.; Matharu, A. S.; Rejsek, K.; Formanek, P. The significance of d -amino acids in soil, fate and utilization by microbes and plants: review and identification of knowledge gaps Plant Soil 2012, 354, 21-39
9. Erikson, O.; Hertzberg, M.; Näsholm, T. A conditional marker gene allowing both positive and negative selection in plants Nat. Biotechnol. 2004, 22, 455-458
10. Erikson, O.; Hertzberg, M.; Näsholm, T. The dsdA gene from Escherichia coli provides a novel selectable marker for plant transformation Plant Mol. Biol. 2005, 57, 425-433
11. Näsholm, T.; Kielland, K.; Ganeteg, U. Uptake of organic nitrogen by plants New Phytol. 2009, 182, 31-48
12. Liardon, R.; Jost, R. Racemization of free and protein-bound amino acids in strong mineral acid Int. J. Pept. Protein Res. 1981, 18, 500-505
13. Liardon, R.; Hurrel, R. Amino acid racemization in heated and alkali-treated proteins J. Agric. Food Chem. 1983, 31, 432-437
14. Ilisz, I.; Berkecz, R.; Peter, A. HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic-based chiral stationary phases: A review J. Sep. Sci. 2006, 29, 1305-1321
15. León, J.; Reubsaet, E.; Beijnen, J. H.; Bult, A.; van Maanen, R. J.; Danielle Marchal, J. A.; Underberg, W. J. M. Analytical techniques used to study the degradation of proteins and peptides: chemical instability J. Pharm. Biomed. Anal. 1998, 17, 955-978
16. Schurig, V. Gas chromatographic enantioseparation of derivatized alpha-amino acids on chiral stationary phases-Past and present J. Chromatogr., B 2011, 879, 3122-3140
17. Sánchez-Hernández, L.; Castro-Puyana, M.; Marina, M. L.; Crego, A. L. Recent approaches in sensitive enantioseparations by CE Electrophoresis 2012, 33, 228-242
18. Poinsot, V.; Carpene, M. A.; Bouajila, J.; Gavard, P.; Feurer, B.; Couderc, F. Recent advances in amino acid analysis by capillary electrophoresis Electrophoresis 2012, 33, 14-35
19. Desiderio, C.; Iavarone, F.; Rossetti, D. V.; Messana, I.; Castagnola, M. Capillary electrophoresis-mass spectrometry for the analysis of amino acids J. Sep. Sci. 2010, 33, 2385-2393
20. Schultz, C. L.; Moini, M. Analysis of underivatized amino acids and their d / l -enantiomers by sheathless capillary electrophoresis/electrospray ionization-mass spectrometry Anal. Chem. 2003, 75, 1508-1513
21. Moini, M.; Schultz, C. L.; Mahmood, H. CE/electrospray ionization-MS analysis of underivatized d / l -amino acids and several small neurotransmitters at attomole levels through the use of 18-crown-6-tetracarboxylic acid as a complexation reagent/background electrolyte Anal. Chem. 2003, 75, 6282-6287
22. Simó, C.; Rizzi, A.; Barbas, C.; Cifuentes, A. Chiral capillary electrophoresis-mass spectrometry of amino acids in foods Electrophoresis 2005, 26, 1432-1441
23. Giuffrida, A.; León, C.; García-Cañas, V.; Cucinotta, V.; Cifuentes, A. Modified cyclodextrins for fast and sensitive chiral-capillary electrophoresis-mass spectrometry Electrophoresis 2009, 30, 1734-1742
24. Yuan, B.; Wu, H.; Sanders, T.; McCullum, C.; Zheng, Y.; Tchounwou, P. B.; Liu, Y.-M. Chiral capillary eliectrophoresis-mass spectrometry of 3,4-dihydroxyphenylalanine: Evidence for its enantioselective metabolism in PC-12 nerve cells Anal. Biochem. 2011, 416, 191-195
25. Zhang, Y.; Huang, L.; Chen, Q.; Chen, Z. A silica monolithic column with chemically bonded l -pipecolic acid as chiral stationary phase for enantiomeric separation of dansyl amino acids by CEC-MS Chromatographia 2012, 75, 289-296
26. 2 method for the enantiomeric separation of l / d -carnitine: Application to the analysis of infant formulas Electrophoresis 2009, 30, 337-348
27. Sánchez-Hernández, L.; Castro-Puyana, M.; García-Ruiz, C.; Crego, A. L.; Marina, M. L. Determination of l-and d -carnitine in dietary food supplements using capillary electrophoresis-tandem mass spectrometry Food Chem. 2010, 120, 921-928
28. Sánchez-Hernández, L.; García-Ruiz, C.; Crego, A. L.; Marina, M. L. Sensitive determination of d -carnitine as enantiomeric impurity of levo-carnitine in pharmaceutical formulations by capillary electrophoresis-tandem mass spectrometry J. Pharm. Biomed. Anal. 2010, 53, 1217-1223
29. Domínguez-Vega, E.; Sánchez-Hernández, L.; García-Ruiz, C.; Crego, A. L.; Marina, M. L. Development of a CE-ESI-ITMS method for the enantiomeric determination of the non-protein amino acid ornithine Electrophoresis 2009, 30, 1724-1733
30. Cavani, L.; Ciavatta, C.; Gessa, C. Determination of free l and d alanine in hydrolysed protein fertilisers by capillary electrophoresis J. Chromatogr., A 2003, 985, 463-469
31. Cohen, S. A.; Michaud, D. P. Synthesis of a fluorescent derivatizing reagent, 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate, and its application for the analysis of hydrolysate amino acids via high-performance liquid chromatography Anal. Biochem. 1993, 211, 279-287
32. Li, H.; Wang, H.; Chen, J.; Wang, L. H.; Zhang, H. S.; Fan, Y. Determination of amino acid neurotransmitters in cerebral cortex of rats administered with baicalin prior to cerebral ischemia by capillary electrophoresis-laser-induced fluorescence detection J. Chromatogr., B 2003, 788, 93-101
33. Pobozy, E.; Czardowska, W.; Trojanowicz, M. Determination of amino acids in saliva using capillary electrophoresis with fluorimetric detection J. Biochem. Biophys. Methods 2006, 67, 37-47
34. Underberg, W. J. M.; Waterval, J. C. M. Derivatization trends in capillary electrophoresis: An update Electrophoresis 2002, 23, 3922-3933
35. D'Orazio, G.; Cifuentes, A.; Fanali, S. Chiral nano-liquid chromatography-mass spectrometry applied to amino acids analysis for orange juice profiling Food Chem. 2008, 108, 1114-1121
36. Reischl, R. J.; Lindner, W. Methoxyquinoline labeling-A new strategy for the enantioseparation of all chiral proteinogenic amino acids in 1-dimensional liquid chromatography using fluorescence and tandem mass spectrometric detection J. Chromatogr., A 2012, 1269, 262-269
37. 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
38. Petritis, K.; Valleix, A.; Elfakir, C.; Dreux, M. Simultaneous analysis of underivatized chiral amino acids by liquid chromatography-ionspray tandem mass spectrometry using a teicoplanin chiral stationary phase J. Chromatogr., A 2001, 913, 331-340
39. Song, Y.; Shenwu, M.; Zhao, S.; Hou, D.; Liu, Y.-M. Enantiomeric separation of amino acids derivatized with 7-fluoro-4-nitrobenzoxadiazole by capillary liquid chromatography/tandem mass spectrometry J. Chromatogr., A 2005, 1091, 102-109
40. Hunt, S. The non-protein amino acids. In Chemistry and biotechnology of the amino acids; Chapman & Hall LTD: 1985; pp 55-137.