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Determination of structure and conformation in solution of syringotoxin, a lipodepsipeptide fromPseudomonas syringae pv.syringae by 2D NMR and molecular dynamics

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Abstract

Strain B427 ofPseudomonas syringae pv.syringae, originally isolated from lemon, produces several bioactive lipodepsipeptides. The structure of Syringotoxin (ST) and Syringopeptins (SPs) has been investigated in these last years. This paper reports the 2D NMR data collected in the study of ST covalent structure. The study was performed in different solvents in order both to prevent aggregation and to completely characterize the side chains features. These include the presence of common and less common aminoacids, which compose the macrocyclic ring and fatty acid side-chain moieties of ST. The nature and position in the molecule of the residues involved in the lactonic ring closure of ST have been identified with certainty. The interpretation of NOE data obtained in acetonitrile/water solution was performed by molecular dynamics calculations in vacuo. This procedure has allowed determination of the nature and number of intramolecular hydrogen bonds and the predominant conformation of ST.

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References

  1. Gross, D. C.; DeVay, J. E.Proc. Am. Phytopathol. Soc. 1976,3, 269–270.

    Google Scholar 

  2. Gross, D. C.; DeVay, J. E.; Stadman, F. H.J. Appl. Bacteriol. 1977,43, 453–486.

    Google Scholar 

  3. Gonzales, C. F.; DeVay, J. E.; Wakeman, R.J. Physiol. Mol. Plant Pathol. 1981,18, 41–50.

    Google Scholar 

  4. Ballio, A.; Bossa, F.; Collina, A.; Gallo, M.; Iacobellis, N. S.; Paci, M.; Pucci, P.; Scaloni, A.; Segre, A.; Simmaco, M.FEBS Lett. 1990,269, 3777–3780.

    Article  Google Scholar 

  5. Ballio, A.; Barra, D.; Bossa, F.; Collina, A.; Grgurina, I., Marino, G.; Moneti, G.; Paci, M.; Pucci, P.; Segre, A. L.; Simmaco, M.FEBS Lett. 1991,291, 109–112.

    Article  PubMed  Google Scholar 

  6. Iacobellis, N. S.; Lavermicocca, P.; Grgurina, I.; Simmaco, M.; Ballio, A.Physiol. Mol. Plant Pathol. 1992,40, 107–116.

    Article  Google Scholar 

  7. Fukuchi. N.; Isogai, A.; Nakayama, J.; Takayama, S.; Yamashita, S.; Suyama, K.; Takemoto, J. Y.; Suzuki, A.J. Chem. Soc. Perkin Trans. 1 1992, 1149–1157.

  8. Gross, K.-H.; Kalbitzer, H. R.J. Magn. Reson. 1988,76, 87–89.

    Google Scholar 

  9. Fukuchi, A.; Isogai, A.; Suzuki, A.Agric. Biol. Chem. 1991,55, 625–627.

    Google Scholar 

  10. Mortishire-Smith, R. J.; Nutkins, J. C.; Packman, L. C.; Brodey, C. L.; Rainey, P. B.; Johnstone, K.; Williams, D. H.Tetrahedron 1991,47, 3645–3654.

    Article  Google Scholar 

  11. Marion, D.; Wüthrich, K.;Biochem. Biophys. Res. Commun. 1983,113, 967–974.

    Article  PubMed  Google Scholar 

  12. Piantini, U.; Sørensen, O. W.; Ernst, R. R.J. Am. Chem. Soc. 1982,104, 6800–6801.

    Article  Google Scholar 

  13. Rance, M.; Sørensen, O. W.; Bodenhausen, G.; Wagner, G.; Ernst, R. R.; Wüthrich, K.Biochem. Biophys. Res. Commun. 1983,117, 479–485.

    Article  PubMed  Google Scholar 

  14. Braunschweiler, L.; Ernst, R. R.J. Magn. Reson. 1983,53, 521–528.

    Google Scholar 

  15. Bax, A.; Davis, D. G.;J. Magn. Reson. 1985,65, 355–360.

    Google Scholar 

  16. Wüthrich, K.; Kogler, G.; Ernst, R. R.;J. Magn. Res. 1984,58, 370–388.

    Google Scholar 

  17. Bothner-By, A. A.; Stephens, R. L.; Lee, J.; Warren, C. D.; Jeanloz, R. W.;J. Am. Chem. Soc. 1984,706, 811–813.

    Article  Google Scholar 

  18. Griesinger, C.; Ernst, R. R.J. Magn. Reson. 1987,75, 261–271.

    Google Scholar 

  19. Boelens, R.; Vuister, G.;Software for Processing Multidimensional NMR Spectra; Utrecht: The Netherlands. (Courtesy of Prof. R. Kaptein).

  20. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; Di Nola, A.; Haak, J. R.J. Chem. Phys. 1984,81, 3684–3690.

    Article  Google Scholar 

  21. Aqvist, J.; van Gunsteren, W. F.; Leijonmarck, M.; Tapia, O.,J. Mol. Biol. 1985,183, 461–477.

    Article  PubMed  Google Scholar 

  22. Kaptein, R.; Zuiderweg, E. R. P.; Scheek, R. M.; Boelens, R.; van Gunsteren, W. F.J. Mol. Biol. 1985,182, 179–182.

    Article  PubMed  Google Scholar 

  23. Kaptein, R.; Boelens, R.; Scheek, R. M.; van Gunsteren, W. F.;Biochemistry 1988,27, 5389–5395.

    Article  PubMed  Google Scholar 

  24. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C.Mol. Phys. 1988,34, 1311–1327.

    Google Scholar 

  25. Berendsen, H. J. C.; van Gunsteren, W. F. InMolecular Liquids. Dynamics and Interactions, Barnes, A. J., et al. Eds.; NATO ASI SeriesC135, Reidel, Dordrecht, pp. 475–500.

  26. Kirkpatrick, S., Gelatt, C. D., Jr. and Vecchi, M. P.Science 1983,220, 671–680.

    Google Scholar 

  27. Bruccoleri, R. E.; Karplus, M.Biopolymers 1990,29, 1847–1862.

    Article  PubMed  Google Scholar 

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Ballio, A., Collina, A., Nola, A.D. et al. Determination of structure and conformation in solution of syringotoxin, a lipodepsipeptide fromPseudomonas syringae pv.syringae by 2D NMR and molecular dynamics. Struct Chem 5, 43–50 (1994). https://doi.org/10.1007/BF02278694

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  • DOI: https://doi.org/10.1007/BF02278694

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