Summary
Methyl esters of the pentafluoropropionyl-amino acid derivatives of the tetrafunctional, sulphur-bridged, stereoisomeric lanthionines, cystathionines and β-methyl-lanthionines were resolved on glass capillaries coated with the chiral stationary phase N-propionyl-L-valine-N-tert-butylamide-polysiloxane (Chirasil-Val) within 35min. Interestingly, L-cystathionine elutes before its D-enantiomer in contrast to the usual order of emergence on an L-phase. The method was applied to the polypeptide antibiotic nisin, which contains mesolanthionine and 2S,3S,6R-3-methyl-lanthionine.
N-Pentafluoropropionyl-S-alkylthiocysteine methyl esters (R=methyl, ethyl, n- and iso-propyl, n- and sec-butyl, n-octyl, neo-pentyl, cyclohexyl-, benzyl-, tolyl-) were separated on Chirasil-Val within 30min. The identity of all derivatives was shown by combined gas chromatography-mass spectrometry.
Similar content being viewed by others
References
J. P. Greenstein, M. Winitz, Chemistry of the Amino Acids, Vol. 3, Wiley, New York 1961.
E. Wünsch (Editor),Houben-Weyl-Müller, Methoden der Organischen Chemie, Vol. XV, Thieme, Stuttgart 1974.
E. Gross, J. L. Morell, J. Am. Chem. Soc.93, 4634 (1971).
T. Wakamiya, K. Shimbo, A. Sano, K. Fukase, H. Yasuda, T. Shiba, in Peptide Chemistry 1982 (S. Sakakibara, Editor) Protein Research Foundation, Osaka 1983, p. 149.
U. Weber, P. Hartter, Z. Physiol. Chem.351, 1384 (1970).
P. Hartter, U. Weber, Z. Physiol. Chem.,354, 365 (1973), and refs. cited therein.
M. Friedman, The Chemistry and Biochemistry of the Sulfhydryl Group in Amino Acids, Peptides and Proteins, Pergamon, Oxford 1973.
P. C. Jocelyn, Biochemistry of the SH Group, Academic, London 1972.
Yu. M. Torchinskii, Sulfhydryl and Disulfide Groups of Proteins, Consultants Bureau, Plenum Publ., New York 1974.
S. Patai (Editor), The Chemistry of the Thiol Group, Wiley, London 1974.
H. Frank, G. J. Nicholson, E. Bayer, Angew. Chem.90, 396 (1978);E. Bayer, Z. Naturforschg.38b, 1281 (1983).
H. Frank, G. J. Nicholson, E. Bayer, J. Chromatogr.146, 197 (1978).
H. Frank, G. J. Nicholson, E. Bayer, J. Chromatogr.167, 187 (1978).
H. Frank, D. Bimboes, G. J. Nicholson, Chromatographia12, 168 (1979).
B. Koppenhöfer, H. Allmendinger, G. J. Nicholson, E. Bayer, J. Chromatogr.260, 63 (1983).
H. Brückner, G. J. Nicholson, G. Jung, K. Kruse, W. A. König, Chromatographia13, 209 (1980);13, 516 (1980).
H. Brückner, G. Jung, Liebigs Ann. Chem. 1982, 1677.
G. Jung, M. Ottnad, M. Rimpler, Eur. J. Biochem.35, 436 (1973).
M. Ottnad, C. Ottnad, P. Hartter, G. Jung, Tetrahedron31, 1155 (1975).
G. Jung, M. Ottnad, Chemiker-Ztg.98, 147 (1974), and inK. Maas (Editor), Themen zur Chemie des Schwefels, Huthig, Heidelberg, 1975, p. 167.
E. Müller (Editor),Houben-Weyl-Müller, Methoden der Organischen Chemie, Vol. 11/2; p. 450, Thieme, Stuttgart 1974; and refs. cited therein.
A. Schöberl, H. Gräffe, Chem. Ber.94, 2583 (1961).
U. Beitler, B. Feibush, J. Chromatogr.123, 149 (1976).
R. Liardon, S. Ledermann, J. of HRC u. CC,3, 475 (1980). and refs. cited therein.
R. Charles, U. Beitler, B. Feibush, E. Gil-Av, J. Chromatogr.112, 121 (1975), and refs. cited therein.
S. Weinstein, G. Jung, E. Gil-Av, Isr. J. Chem.9, 202 (1971).
J. L. Morell, E. Gross, J. Am. Chem. Soc.95, 6480 (1973).
U. Weber, P. Hartter, L. Flohé, Hoppe-Seyler's Z. Physiol. Chem.351, 1389 (1970).
U. Weber, Hoppe-Seyler's Z. Physiol. Chem.350, 1421 (1969).
E. Wünsch, L. Moroder, S. Romani, Hoppe-Seyler's Z. Physiol. Chem.363, 1461 (1982).
E. Bayer, E. Küsters, G. J. Nicholson, H. Frank, manuscript in preparation.
E. Küsters, doctoral thesis, University of Tübingen, 1983.
L. Moroder, E. Wünsch, N. Vaysse, A. Ribet, Hoppe-Seyler's Z. Physiol. Chem.363, 1247 (1982).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Küsters, E., Allgaier, H., Jung, G. et al. Resolution of sulphur-containing amino acids by chiral phase gas chromatography. Chromatographia 18, 287–293 (1984). https://doi.org/10.1007/BF02259079
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02259079