Abstract
A new method has been developed to identify the isomers of amino acids by derivatization of the corresponding standards with 1-fluoro-2,4-dinitrophenyl-5-l-alanine amide (Marfey’s reagent or FDAA) and analysis of the diastereomeric derivatives by a liquid chromatography-thermospray mass spectrometry technique. Quantification of the FDAA derivatives that originate from standards was possible by using l-phenylalanine as the internal standard. The procedure was applied to determine the chiralities of the amino acids present in some previously uncharacterized blue-green algal peptides (microcystins).
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Botes, D. P.; Viljoen, C. C.; Kruger, H.; Wessels, P. L. Toxicon 1982, 20, 1037–1042.
Botes, D. P.; Tuinman, A. A.; Wessels, P. L.; Viljoen, C. C.: Kruger, H.; Williams, D. H.; Santikam, S.; Smith, R. J.; Hammond, S. J. Chem. Soc., Perkin Trans. 1984, 2311–2318.
Krishnamurthy, T.; Szafraniec, L.; Hunt, D. F.; Shabanowitz, J.; Yates, III, J. R.; Haeur, C. R.; Carmichael, W. W.; Skulberg, O.; Codd, G. A.; Missler, S. Proc. Nat. Acad. Sci. USA 1989, 86, 770–774.
Gathercole, P. S.; Thiel, P. G. J. Chromatog. 1987, 408, 435–440.
Carmichael, W. W. J. Appl. Bact. 1992, 72, 445–459.
Sivonen, K.; Namikoshi, M.; Evans, W. E.; Fardig, M.; Carmichael, W. W.; Rinehart, K. L. Chem. Res. Toxicol. 1992, 5, 464–469.
Namikoshi, M.; Rinehart, K. L.; Saka, R.; Slotts, R. R.; Dahlem, A. M.; Beasley, V. R.; Carmichael, W. W.; Evans, W. R. J. Org. Chem. 1992, 57, 866–872.
Rinehart, K. L.; Harada, K. I.; Namikoshi, M.; Chen, C.; Harvis, C. A.; Munro, M. H. G.; Blunt, J. W.; Mulligan, P. E.; Beasley, V. R.; Dahlem, A. M.; Carmichael, W. W. J, Am. Chem. Soc. 1988, 110, 8557–8558.
Namikoshi, M.; Rinehart, K. L.; Dahlem, A. M.; Beasley, V. A.; Carmichael, W. W. Tetrahedron Lett. 1989, 30, 4349–4352.
Carmichael, W. W.; Krishnamurthy, T.; Beasley, V. A.; Min-Juan, Y.; Bunner, D. L.; Moore, J. E.; Eloff, J. N.; Rinehart, K. L.; Falconer, I.; Runnegar, M.; Gorham, P.; Skulberg, O. M.; Harada, K.; Watanabi, M. Toxicon 1988, 26, 971–973.
Marfey, P. Carlsberg Res. Commun. 1984, 49, 591–596.
Nambara, T. In CRC Handbook of HPLC for the Separation of Amino Acids, Peptides, and Proteins; Hancock, W. S., Ed.; CRC Press: Boca Raton, FL, 1984; Vol. 1, pp. 383–389.
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Krishnamurthy, T. Chirality in microcystins. J Am Soc Mass Spectrom 5, 724–730 (1994). https://doi.org/10.1016/1044-0305(94)80004-9
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DOI: https://doi.org/10.1016/1044-0305(94)80004-9