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HPLC Derivatization Reagents
NBD- and DBD-derivatives developed by Imai, Toyo’oka and co-workers are excellent fluorescent labeling reagents with strong and long wave-length fluorescence resulting from their benzoxadiazole skeleton and they are used for analysis of various biological substances. NBD-Cl was the earliest fluorescence reagent which was applied to HPLC and its effectiveness for the secondary amines, such as proline, was reported. Imai and co-workers developed NBD-F1), in which the chlorine was replaced with fluorine, for HPLC analysis and obtained good results. Also, they developed DBD-F2) where a dimethylsulfamoyl group was introduced into the benzoxadiazole skeleton and used it for the analysis of amino acids by reversed phase HPLC. Because DBD-F itself is non-fluorescent, DBD-labeled amino acids can be detected and analyzed with high sensitivity. DBD-COCl3) reacts with a hydroxy group as well as amines and thiols, and forms a stable fluorescence adduct. In addition, NBD- and DBD-H4), in which a hydrazino group is introduced into the NBD-, DBD- skeleton, are used for analysis of carbonyl groups. NBD- and DBD-PZ5), in which a piperazino group is introduced, are used for analysis of carboxyl groups.
- 1)(a) K. Imai, Y. Watanabe, Anal. Chim. Acta 1981, 130, 377.
- 2)(a) T. Toyo'oka, T. Suzuki, Y. Saito, S. Uzu, K. Imai, Analyst 1989, 114, 413.
- 3)(a) K. Imai, T. Fukushima, H. Yokosu, Biomed. Chromatogr. 1994, 8, 107.
- (b) Tokyo Kasei Kogyo Co., Ltd., Jpn. Kokai Tokkyo Koho 7 238075, 1995.
- 4)S. Uzu, S. Kanda, K. Imai, K. Nakashima, S. Akiyama, Analyst 1990, 115, 1477.
- 5)T. Toyo’oka, M. Ishibashi, Y. Takeda, K. Nakashima, S. Akiyama, S. Uzu, K. Imai, J. Chromatogr. 1991, 588, 61.
- 6)NPCA : Succinimidyl (2R)-6-(Tetrahydro-2H-pyran-2-yloxy)-2,5,7,8-tetramethylchroman-2-carboxylate
- 7)T. Kawasaki, M. Maeda, A. Tsuji, J. Chromatogr. 1985, 328, 121.