Summary
The structural identity of the polypeptide antibiotics, samarosporin I(II) and stilbellin I(II) with emerimicin IV(III) has been established by thin-layer chromatography, quantitative amino acid analysis by ion-exchange chromatography, gas-liquid chromatography of the N-pentafluoropropionyl amino acid n-propyl esters and N,O-bis-pentafluoropropionyl phenylalaninol with quartz capillaries coated with the chiral stationary phase N-propionyl-L-valine-tert-butylamide, and determination of the relative molecular masses and sequence-specific fragments by field desorption fast atom bombardment mass spectrometry. The separation of closely related sequence analogues of the above polypeptides could be achieved by reversed-phase high-performance liquid chromatography with spherical, fully porous octadecylsilyl bonded phases, and 86% aqueous methanol as eluent. The application of both chromatographic and mass spectrometric methods is demonstrated to be most valuable for the characterization of antibiotics with the unusual constituents α-aminoisobutyric acid, isovaline and phenylalaninol. The methology employed is regarded to be applicable to all polypeptide antibiotics of the peptaibol class.
Similar content being viewed by others
References
For a collection of references see:H. Brückner, G. J. Nicholson, G. Jung, K. Kruse, W.A. König, Chromatographia13, 209 (1980); correction: ibidH. Brückner, G. J. Nicholson, G. Jung, K. Kruse, W. A. König Chromatographia13, 516 (1980).
For a review see:G. Jung, H. Brückner, H. Schmitt, in „Structure and Activity of Natural Peptides”,W. Voelter, G. Weitzel, eds., De Gruyter, Berlin, 1981; p. 75.
H. Brückner, H. Graf, Experientia39, 528 (1983).
R. C. Pandey, H. Meng, J. C. Cook, K. L. Rinehart, J. Amer. Chem. Soc.99, 5203 (1977).
D. A. Bullough, C. G. Jackson, P. J. F. Henderson, R. B. Beechey, P. E. Linnett, FEBS Letters145, 258 (1982).
T. Fujita, Y. Takaishi, A. Okamura, J. Chem. Soc., Chem. Commun.1981, 585.
Y. Mori, M. Tsuboi, M. Suzuki, K. Fukushima, T. Arai, J. Chem. Soc., Chem. Commun.1982, 94.
G. Irmscher, G. Jung, Eur. J. Biochem.80, 165 (1977).
H. Brückner, G. Jung, Chromatographia13, 170 (1980).
E. Katz, G. Jung, M. Aydin, W. A. König, manuscript submitted.
T. Fujita, Y. Takaishi, T. Shiromoto, J. Chem. Soc., Chem. Commun.1979, 413.
H. Brückner, G. Jung, Liebigs Ann. Chem.1982, 1677.
A. D. Argoudelis, L. E. Johnson J. Antibiot.27, 274 (1974).
K. L. Rinehart, L. A. Gaudioso, M. L. Moore, R. C. Pandey, J. C. Cook, M. Barber, R. D. Sedgwick, R. S. Bordoli, A. N. Tyler, B. N. Green, J. Amer. Chem. Soc.103, 6517 (1982).
M. J. Thirumalachar, Hindustan Antibiot. Bull.10, 287 (1968).
N. Inoue, A. Inoue, M. Furukawa, N. Kanda, J. Antibiot.29, 618 (1976).
K. Sasaki, H. Minato, K. Katagiri, S. Hayakawa, T. Matsushima, J. Antibiot.24, 67 (1971).
R. C. Pandey, J. C. Cook, K. L. Rinehart, J. Amer. Chem. Soc.99, 5205 (1977).
R. Bosch, H. Brückner, G. Jung, W. Winter, Tetrahedron38, 3579 (1982).
R. C. Pandey, J. C. Cook, K. L. Rinehart, J. Antibiot.31, 241 (1978).
H. Brückner, H. Graf, M. Bokel, Experientia, accepted.
M. Przybylski, Z. Anal. Chem.315, 402 (1983).
K. L. Rinehart, J.C. Cook, H. Meng, K. L. Olson, R. C. Pandey, Nature269, 832 (1977).
A. Buko, L. R. Phillipps, B. A. Fraser, Biomed. Mass. Spectrom.10, 387 (1983).
M. Przybylski, I. Manz, I. Dietrich, K. H. Maurer. Z. Anal. Chem., in press.
D. H. Williams, C. V. Bradley, S. Santikarn, G. Bojesen, Biochem. J.201, 105 (1982).
H. Frank, G. J. Nicholson, E. Bayer, J. Chrom. Sci.15, 174 (1977).
G. Jung, H. Brückner, Hoppe-Seyler's Z. Physiol. Chem.362, 291 (1981).
C. Toniolo, G. M. Bonora, A. Bavoso, E. Benedetti, B. di Blasio, V. Pavone, C. Pedone, Biopolymers 22, 205 (1983).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Brückner, H., Jung, G. & Przybylski, M. Chromatographic and mass spectrometric characterization of the structures of the polypeptide antibiotics samarosporin and stilbellin and identity with emerimicin. Chromatographia 17, 679–685 (1983). https://doi.org/10.1007/BF02259320
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02259320