Review: Liquid chromatographypost-column derivatization for amino acid analysis: Strategies, instrumentation, and applications

Instrumentation Science and Technology

Volumn 40, Issue 2-3, 2012, Pages 161-193

  Rigas, Pantelis G ^a  

^a ALEXANDER TECHNOLOGICAL EDUCATIONAL INSTITUTE OF THESSALONIKI   (Greece)

Author keywords

amino acid analysis; ion exchange chromatography; post column derivatization

Indexed keywords

ACID SEPARATION; AMINO ACID ANALYSIS; BIOLOGICAL FLUIDS; CHROMATOGRAPHIC METHODS; CHROMATOGRAPHIC TECHNIQUES; CLINICAL ANALYSIS; DERIVATIZATIONS; INSTRUMENTATION TECHNOLOGIES; ION-EXCHANGE CHROMATOGRAPHY; POST-COLUMN; POST-COLUMN DERIVATIZATION; SEPARATION TECHNIQUES;

CHROMATOGRAPHIC ANALYSIS; LIQUID CHROMATOGRAPHY; SEPARATION; TISSUE;

AMINO ACIDS;

EID: 84862104971     PISSN: 10739149     EISSN: 15256030     Source Type: Journal    
DOI: 10.1080/10739149.2011.651669     Document Type: Review

References (99)

1. Moore, S.; Stein, W. H. Chromatography of amino acids on sulfonated polystyrene resins. J. Biol. Chem. 1951, 192, 663-681.
2. Moore, S.; Stein, W. H. Chromatographic determination of amino acids by the use of automatic recording equipment. Methods Enzymol. 1963, 6, 819-831.
3. Spackman, H. D.; Stein, H. W.; Moore, S. Automatic recording apparatus for use in chromatography of amino acids. Anal. Chem. 1958, 30(7), 1190-1206.
4. Ashworth, B. R. Ion-exchange separation of amino acids with postcolumn orthophthalaldehyde detection. J. Assoc. Off. Anal. Chem. 1987, 70, 248-252.
5. Grunau A. J.; Swiader, M. J. Chromatography of 99 amino acids and other ninhydrinreactive compounds in the Pickering lithium gradient system. J. Chromatogr. 1992, 594, 165-171.
6. Aruda, O. W.; Aruda, O. K. Review of volatile perfluorocarboxylic acids as ion pair reagents in LC: Part I. LC-GC North America 2009, 27(10), 916-929.
7. Aruda, O. W.; Aruda, O. Review of volatile perfluorocarboxylic acids as ion pair reagents in LC: Part II. LC-GC North America 2009, 27(8), 626-636.
8. Pickering, V. M. Ion exchange chromatography of free amino acids. LC-GC, 1989, 7(6), 484-490.
9. Samejima, K. Separation of fluorescamine derivatives of aliphatic diamines and polyamines by high-speed liquid chromatography. J. Chromatogr. 1974, 96, 250-254.
10. Zacharis, K. C.; Tzanavaras, F. P.; Mouroutis, N. P.; Rigas, G. P. NBD-Cl as a post column reagent for primary and secondary amines after separation by ion exchange chromatography. Anal. Lett., 2011, 44, 1-15.
11. Imai, K.; Watanabe, Y. Fluorimetric determination of secondary amino acids by 7-fluoro-4- nitrobenzo-2-oxa-1,3-diazole. Anal. Chim. Acta 1981, 130, 377-383.
12. Deyl, Z.; Hyanek, J.; Horakova, M. Profiling of amino acids in body fluids and tissues by means of liquid chromatography. J. Chromatogr. 1986, 379, 177-250.
13. Fukushima, T.; Usui, N.; Santa, T.; Imai, K. Recent progress in derivatization methods for LC and CE analysis. J. Pharm. Biomed. Anal., 2003, 30, 1655-1687.
14. Husek, P.; Simek, P. Advances in amino acid analysis. LC-GC 2001, 19(9), 986-999.
15. Anders, C. J. Advances in amino acid analysis. BioPharm 2002, April, 32-39.
16. Peace, W. R.; Gilani, S. G. Chromatographic determination of amino acids in foods. J. AOAC Int. 2005, 88, 877-887.
17. Papadoyannis, N. I.; Theodoridis, A. G. HPLC Analysis of Amino Acids, Encyclopedia of Chromatography, 3rd ed.; J. Cazes (Ed.); CRC Press: Boca Raton, FL, 2010; 67-72.
18. Coppex, L. Derivatives for HPLC Analysis. 2000. Available from: http://www.sigmaaldrich.com/img/assets/22084/HPCL-Derivatization-Literature.pdf
19. Toyo'oka, T. Ed. Modern Derivatization Methods for Separation Sciences; John Wiley: New York, 1999.
20. Csapo, J.; Albert, C.; Loki, K.; Csapo-Kiss, Z. Separation and determination of the amino acids by ion exchange column chromatography applying postcolumn derivatization. Acta Univ. Sapientiae, Alimentaria 2008, 1, 5-29.
21. Welch, E. L.; LaCourse, R. W.; Mead Jr., D. A.; Johnson, C. D.; Hu, T. Comparison of pulsed coulometric detection and potential-sweep-pulsed coulometric detection for underivatized amino acids in liquid chromatography. Anal. Chem. 1989, 61(6), 555-559.
22. Adriaens, P.; Meesschaert, B.; Wuyts, W.; Vanderhaeghe, H.; Eyssen, H. Separation of ninhydrinpositive compounds on a single-column amino acid analyzer using lithium buffers. J. Chromatogr. 1977, 40, 103-108.
23. Yokoyama, Y.; Wakabayashi, N.; Furugaki, Y.; Sato, H. Low-capacity cation-exchange chromatography of amino-acids using a novel sulfoacylated macroreticular polystyrenedivinylbenzene column with binary gradient elution. Anal. Sci. 2004, 20(8), 1189-1192.
24. Clarke, P. A.; Jandik, P.; Rocklin, D. R.; Liu, Y.; Avdalovic, N. An integrated amperometry waveform for the direct, sensitive detection of amino acids and amino sugars following anionexchange chromatography. Anal. Chem. 1999, 71, 2774-2781.
25. Jandik, P.; Cheng, J.; Jensen, D.; Manz, S.; Avdalovic, N. Simplified in-line sample preparation for amino acid analysis in carbohydrate containing samples. J. Chromatogr. 2001, 758, 189-196.
26. Hanko, P. V.; Heckenberg, A.; Rohrer, S. J. Determination of amino acids in cell culture and fermentation broth media using anion-exchange chromatography with integrated pulsed amperometric detection. J. Biomol. Techn. 2004, 15, 317-324.
27. Rigas, G. P.; Arvanitis, J. S.; Pietrzyk, J. D. Ion interaction chromatographic separation of amino acids using a basic-tetraalkylammonium salt mobile phase. J. Liq. Chromatogr. 1987, 10(13), 2891-2910.
28. Walker A. T.; Pietrzyk, J. D. Ion-interaction chromatographic separation of free amino acids. J. Liq. Chromatogr. 1987, 10(1), 161-174.
29. Yokoyama, Y.; Amaki, T.; Horikoshi, S.; Sato, H. Optimum combination of reversed-phase column type and mobile-phase composition for gradient elution ion-pair chromatography of amino acids. Anal. Sci. 1997, 13, 963-967.
30. Pappa-Louisi, A.; Agrafiotou, P.; Papachristos, K. Retention modeling under organic modifier gradient conditions in ion-pair reversed-phase chromatography: Application to the separation of a set of underivatized amino acids. Anal. Bioanal. Chem. 2010, 397, 2151-2159.
31. Petritis, N. K.; Chaimbault, P.; Elfakir, C.; Dreux, M. Ion-pair reversed-phase liquid chromatography for determination of polar underivatized amino acids using perfluorinated carboxylic acids as ion pairing agent. J. Chromatogr. A 1999, 833, 147-155.
32. Chaimbault, P.; Petritis, N. K.; Elfakir, C.; Dreux, M. Ion-pair chromatography on a porous graphitic carbon stationary phase for the analysis of twenty underivatized protein amino acids. J. Chromatogr. A 2000, 870, 245-254.
33. Yokoyama, Y.; Ozaki. O.; Sato. H. Separation and determination of amino acids, creatinine, bioactive amines and nucleic acid bases by dual-mode gradient ion-pair chromatography. J. Chromatogr. A 1996, 739, 333-342.
34. Kaspar, H.; Dettmer, K.; Gronwald, W.; Oefner, J. P. Advances in amino acid analysis. Anal. Bioanal. Chem. 2009, 393, 445-452.
35. Ng, T. L.; Wong, Y. D.; Francis, T.; Anderson, G. H. Ion-exchange chromatography for physiological fluid amino acid analysis. J. Nutr. Biochem. 1991, 2, 671-679.
36. Le Boucher, J.; Charret, C.; Coudray-Lucas, C.; Giboudeau, J.; Cynober, L. Amino acid determination in biological fluids by automated ion-exchange chromatography: Performance of Hitachi L-8500A. Clin. Chem. 1997, 43(8), 1421-1428.
37. Pickering Labs. Amino acid analysis with temperature and eluant gradients. Available from: http://www.pickeringlabs.com/catalog/M-365.asp.
38. Furst, P.; Pollack, L.; Graser, A. T.; Godel H.; Stehle, P. Appraisal of four pre-column derivatization methods for the high-performance liquid chromatographic determination of free amino acids in biological materials. J. Chromatogr. 1990, 499, 557-569.
39. Fierabracci, V.; Masiello, P.; Novelli, M.; Bergamini, E. Application of amino acid analysis by high-performance liquid chromatography with phenyl isothiocyanate derivatization to the rapid determination of free amino acids in biological samples. J. Chromatogr. 1991, 570, 285-291.
40. Fekkes, D.; van Dalen, A.; M. Edelman, M.; Voskuilen, A. Validation of the determination of amino acids in plasma by high-performance liquid chromatography using automated precolumn derivatization with o-phthaldialdehyde. J. Chromatogr., B 1995, 669, 177-186.
41. Fekkes, D. State-of-the-art of high-performance liquid chromatographic analysis of amino acids in physiological samples. J. Chromatogr. B, 1996, 682, 3-22.
42. Qureshia, A. G.; Qureshia, R. A. Determination of free amino acids in biological samples: Problems of quantitation. J. Chromatogr. 1989, 491, 281-289.
43. Schuster, R. Determination of free amino acids by high performance liquid chromatography. Anal. Chem. 1980, 52, 617-620.
44. Hanczká, R.; Jámbora, A.; Perlb, A.; Molnár-Perla,I. Advances in the o-phthalaldehyde derivatizations: Comeback to the o-phthalaldehyde-ethanethiol reagent. J. Chromatogr. A 2007, 1163, 25-42.
45. Irvine, J. B.; Davinson, I. Amino acid analysis: Precolumn derivatization methods. In Molecular Biology 211: Protien Sequencing Protocols, 2nd Ed.; J. B. Smith (Ed.); Humana Press Inc.: Totowa, NJ, 2003; p. 123-131.
46. Smith, J. A. Post column amino acid analysis. In Methods in Molecular Biology 211: Protein Sequencing Protocols, 2nd ed.; J. B. Smith (Ed.); Humana Press Inc.: Totowa, NJ, 2003; p. 133-141.
47. Chow, J.; Orenberg, J. B.; Nugent, K. D. Comparison of automated pre-column and post-column analysis of amino acid oligomers. J. Chromatogr. 1987, 386, 243-249.
48. Friedman, M. Applications of the ninhydrin reaction for analysis of amino acids, peptides, and proteins to agricultural and biomedical sciences. J. Agric. Food Chem. 2004, 52, 385-406.
49. Pickering Labs, Trione® Ninhydrin reagent-Chromatographic Grade™. A prepared reagent for automated post column derivatization of primary and secondary amines. Available from: http://www.pickeringlabs.com/ catalog/RC-TNR.asp.
50. Roth, M. Fluorescence reaction for amino acids, Anal. Chem., 1971, 43, 880-882.
51. Massom, L. R. Amino acid analysis. In Methods of Analysis for Functional Foods and Nutraceuticals; W. J. Hurst (Ed.); CRC Press: New York, NY, 2002; 243-273.
52. Jones, B. N. Amino acid analysis by o-phthaldialdehyde precolumn derivatization and reversephase HPLC. In Methods of Protein Microcharacterization; J. E. Shiveley (Ed.), Humana Press Inc.: Clifton, NJ, 1986; 121-151.
53. Pan, Y. E.; Stein, S. Amino acid analysis with postcolumn fluorescent derivatization. In Methods of Protein Microcharacterization; J. E. Shively (Ed.); Humana Press Inc.: Clifton, NJ, 1986; 105-119.
54. Böhlen, P.; Mellet, M. Automated fluorometric amino acid analysis: The determination of proline and hydroxyproline. Anal. Biochem. 1979, 94, 313-321.
55. Fiorino, A.; Frigo, G.; Cucchetti, E. Liquid chromatographic analysis of amino and imino acids in protein hydrolysates by post-column derivatization with o-phthalaldehyde and 3-mercaptopropionic acid. J. Chromatogr. 1989, 476, 83-92.
56. De Montigny, P.; Stobaugh, F. J.; Givens, S. R.; Carlson, G. R.; Srinivasachar, K.; Sternson, A. L.; Higuchi, T. Naphthalene-2,3- dicarboxyaldehyde/cyanide ion: A rationally designed fluorogenic reagent for primary amines. Anal. Chem. 1987, 59, 1096-1101.
57. Koning, H.; Wolf, H.; Venema, K.; Korf, J. Automated precolumn derivatization of amino acids, small peptides, brain amines and drugs with primary amino groups for reversed-phase highperformance liquid chromatography using naphthalenedialdehyde as the fluorogenic label. J. Chromatogr. 1990, 553, 171-178.
58. Beale, S.; Hsieh, Y.-Z.; D. Wiesler, D.; Novotny, M. Application of 3-(2-furoyl)quinoline-2- carbaldehyde as a fluorogenic reagent for the analysis of primary amines by liquid chromatography with laser-induced fluorescence detection. J. Chromatogr. 1990, 499, 579-587.
59. Beale, S.; Savage, J.; Wiesler, D.; Wietstock, S.; Novotny, M. Fluorescence reagents for high-sensitivity chromatographic measurements of primary amines. Anal. Chem. 1988, 60, 1765-1769.
60. Liu, J.; Hsieh, Y.-Z.; Wiesler, D.; Novotny, M. Design of 3-(4-carboxybenzoyl)-2- quinolinecarboxaldehyde as a reagent for ultrasensitive determination of primary amines by capillary electrophoresis using laser fluorescence detection. Anal. Chem. 1991, 63, 408-412.
61. Udenfriend, S.; Stein, S.; Bohlen, P.; Dairman, W.; Leimgruber, W.; Wieble, M. Fluorescamine: A reagent for assay of amino acids, peptides, proteins, and primary amines in the picomole range. Science 1972, 178(4063), 871-872.
62. Stein, S.; Bohlen, P.; Stone, J.; Dairman, W.; Udenfriend, S. Amino acid analysis with fluorescamine at the picomole level. Arch. Biochem. Biophys. 1973, 155, 202-212.
63. Weigele, M.; DeBernardo, S.; Leimgruber, W. Fluorometric assay of secondary amino acids. Biochem. Biophys. Res. Commun. 1973, 50(2), 352-356.
64. Felix, A. M.; Terkelsen, G. Total fluorometric amino acid analysis using fluorescamine. Arch. Biochem. Biophys. 1973, 157(1), 177-182.
65. Huff, T.; Miller, C.; Hannappel, E. HPLC and post-column derivatization with fluorescamine: Isolation of actin-sequestering/3-thymosins by reversed-phase HPLC. Anal. Chim. Acta 1997, 352, 239-248.
66. Benson, R. J.; Hare, E. P. o-Phthalaldehyde: Fluorogenic detection of primary amines in the picomole range. Comparison with fluorescamine and ninhydrin. Proc. Nat. Acad. Sci. USA 1975, 72(2), 619-622.
67. Saurina, J.; Hernhdez-Cassou, S. Determination of amino acids by ion-pair liquid chromatography with post-column derivatization using 1,2-naphthoquinone-4-sulfonate. J. Chromatogr. A 1994, 676, 311-319.
68. Watanabe, Y.; Imai, K. Liquid chromatographic determination of amino and imino acids and thiols by postcolumn derivatization with 4-fluoro-7-nitrobenzo- 2,1,3-oxadiazole. Anal. Chem. 1983, 55, 1786-1791.
69. Imai, K.; Watanabe, Y.; Toyo'oka, T. Fluorometric assay of amino acids and amines by use of 7-fluoro-4-nitrobenzo-2-oxa-1,3-diazole (NBD-F) in high-performance liquid chromatography. Chromatographia 1982, 16, 214-215.
70. Yoshida, H.; Toshihiko Sumida, T.; Masujlma, T.; lmai, H. Post-column fluorometric detection of amino acids with 7-chloro-4-nitrobenzo-2-oxa-1,3- diazole (NBD-CI)-A sensitive method especially suitable for proline and hydroxyproline. Journal of High Resolution Chromatography & Chromatography Communications 1982, 5, 509-511.
71. Zacharis, K. C.; Tzanavaras, D. P.; Mouroutis, N. P.; Nikolaidis, G.; Rigas, G. P. NBD-Cl as a new post-column reagent for HPLC analysis of primary and secondary amines and amino acids. In Proceedings of the 7th Analytical Chemistry Days AACD 2010, Lesvos, Greece, Sept. 29-Oct. 3, 2010, Book of Abstracts, 2010, 48 p.
72. Roth, M. Fluorimetric determination of free hydroxyproline and proline in plasma. Clin. Chim. Acta 1978, 83, 273-277.
73. Toyo'oka, T.; Suzuki, T.; Saito, Y.; Uzu, S.; Imai, K. Fluorogenic reagent for thiols: 4-(N,NDimethylaminosulphonyl)- 7-fluoro-2,1,3- benzoxadiazole. Analyst 1989, 114, 413-419.
74. Huang, Y.; Matsunaga, H.; Toriba, A.; Santa, T.; Fukushima, T,; Imai, I. Detection of DBDcarbamoyl amino acids in amino acid sequence and configuration determination of peptides with fluorogenic Edman reagent 7-[(N,N dimethylamino)sulfonyl]-2,1,3-benzoxadiazol-4-yl isothiocyanate. Anal. Biochem. 1999, 270(2), 257-267.
75. Imai, K.; Fukushima, T.; Yokosu, H. A novel electrophilic reagent, 4-(N-chloroformylmethyl-Nmethyl) amino-7-N,N-dimethylaminosulphonyl-2,1,3- benzoxadiazole (DBD-COCl) for fluorometric detection of alcohols, phenols, amines and thiols. Biomed. Chromatogr. 1994, 8(3), 107-113.
76. Dou, L.; Krull, S. I. Determination of aromatic and sulfur-containing amino acids, peptides, and proteins using high-performance liquid chromatography with photolytic electrochemical detection. Anal. Chem. 1990, 62(23), 2599-2606.
77. Dou, L.; Krull, S. I. Post-column detection by on-line photolysis-electrochemistry in liquid chromatography-application to the determination of phenylalanine in human urine. J. Pharm. Biomed. Anal. 1990, 8(6), 493-498.
78. Galletti C. G.; Bocchini, P. High-performance liquid chromatography with electrochemical detection of aspartame with a post-column photochemical reactor. J. Chromatogr. A 1996, 729, 393-398.
79. Kaufman, D. A.; Kissinger, T. P.; Jones, E. J. The use of titanium dioxide as a photo-catalyst to improve the sensitivity of post-column photolysis-electrochemical detection for microbore liquid chromatography. Anal. Chim. Acta 1997, 356, 177-186.
80. Liu, H.; Duda, T. C.; Tiehua Huang, T.; Aruda, O. W.; Kissinger, T. P. Optimization of postcolumn photolysis and electrochemical detection for the liquid chromatographic determination of 3-nitro-L-tyrosine. J. Chromatogr. A 1998, 818, 69-75.
81. Fedorowski, J.; LaCourse, R. W. A review of post-column photochemical reaction systems coupled to electrochemical detection in HPLC. Anal. Chim. Acta 2010, 657, 1-8.
82. Pickering, V. M. Assembling an HPLC post column system: Practical considerations. LC-GC 1989, 11(6), 994-997.
83. Maroulis, M.; Monemvasios, I.; Vardaka, E.; Rigas, P. Determination of domoic acid in mussels by HPLC with post-column derivatization using 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl) and fluorescence detection. J. Chromatogr. B 2008, 876(2), 245-251.
84. Frei, W. R. Reaction detectors in modern liquid chromatography. Chromatographia 1982, 15(3), 161-166.
85. Stewart, T. J. Post column derivatization methodology in high performance liquid chromatography (HPLC). Trends Anal. Chem. 1982, 1(7), 170-174.
86. Frei, W. R. Reaction detectors in liquid chromatography. In Chemical Derivatization in Analytical Chemistry; W. R. Frei and F. J. Lawrence (Eds); Plenum Press: New York, 1981; 211-340.
87. Pickering, V. M. Modifying HPLC equipment to tolerate corrosive solutions. LC-GC 1988, 6(9), 800-809.
88. Sarwar, G.; Botting, G. H. Evaluation of liquid chromatographic analysis of nutritionally important amino acids in food and physiological samples. J. Chromatogr. 1993, 615, 1-22.
89. Ravindran, G.; Bryden, W. L. Tryptophan determination in proteins and feedstuffs by ion exchange chromatography. Food Chem. 2005, 89, 309-314.
90. Allard, P.; Cowell, D. L.; Thomas, H.; Zytkovicz, H. T.; Korson, S. M.; Ampola, G. M. Determination of phenylalanine and tyrosine in dried blood specimens by ion-exchange chromatography using the Hitachi L-8800 analyzer. Clin. Biochem. 2004, 37, 857-862.
91. Reilly, A. A.; Bellisario, R.; Pass, A. K. Multivariate discrimination for phenylketonuria (PKU) and non-PKU hyperphenylalaninemia after analysis of newborns' dried blood-spot specimens for six amino acids by ion-exchange chromatography. Clin. Chem. 1998, 44, 317-326.
92. Qu, Y.; Slocum, H. R.; Fu, J.; Rasmussen, E. D.; Rector, H. D.; Miller, B. J.; Coldwell, G. J. Quantitative amino acid analysis using a Beckman system gold HPLC 126AA analyzer. Clin. Chim. Acta 2001, 312, 153-162.
93. Schadewaldt, P.; Bodner-Leidecker, A.; Hammen, H.-W.; Wendel, U. Significance of L-alloisoleucine in plasma for diagnosis of maple syrup urine disease. Clin. Chem. 1999, 45(10), 1734-1740.
94. Ronald, J.; Whitley, J. R.; Hannon, W. H.; Dietzen, J. D.; Rinaldo, P. Pre-analytical, analytical, and post-analytical issues related to follow-up testing of positive newborn screens. In Laboratory Medicine Practice Guidelines, Follow-up Testing for Metabolic Diseases Identified by Expanded Newborn Screening Using Tandem Mass Spectrometry; M. Bennet (Ed.); The National Academy of Clinical Biochemistry, American Association for Clinical Chemistry, Inc.: Washington, DC, 2008; 9-29.
95. INGOS. Amino acid analyser AAA 400. User manual, INGOS: Prague, 2006.
96. INGOS. Collections of examples of analyses. Available at: http://www.instruments.ingos.cz/files/analysis/analyzy-en.pdf.
97. Pickering Labs. Application Manual. Amino Acids; Pickering Labs: Mountain View, California, 2002.
98. Biochrom. Available from http://www.biochrom.co.uk/subcategory/9/ biochrom-30plus-series-ofamino- acid-analyzers.html.
99. Pickering Labs, 30-Minute amino acid analysis of hydrolyzed samples. Available from: http://www.pickeringlabs.com/lib/appnotes/MA380-Fast-AAA.pdf.