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Molecular modeling on garuganin-I

Molekulares Modelling von Garuganin-I

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

The conformation of garuganin-I was analyzed in terms of the mobility of the cyclic structure. Molecular mechanics calculations were applied to show that the interconversion of the optical isomers is not possible at room temperature due to steric interactions. Different possibilities of the distortion of the molecular conformations were calculated and compared with molecular dynamics simulations.

Zusammenfassung

Die Konformation von Garuganin-I wurde bezüglich der Mobilität der cyclischen Struktur analysiert. Es wurden molekularmechanische Berechnungen herangezogen, die zeigten, daß die Interkonversion der optischen Isomeren bei Raumtemperatur wegen sterischer Wechselwirkungen nicht möglich ist. Es wurden verschiedene Möglichkeiten von Konformationsänderungen berechnet und mit einer Simulation der Molekulardynamik verglichen.

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References

  1. Pattabhi V., Krishnaswami S. (1984) Acta Cryst.C 40: 832

    Google Scholar 

  2. Haribal M. N., Mishra A. K., Sabata B. K. (1985) Tetrahedron21: 4949

    Google Scholar 

  3. Kalchhauser H., Krishnamurty H. G., Talukdar A. C., Schmid W. (1988) Monatsh. Chem.119: 1047

    Google Scholar 

  4. Kalchhauser H., Krishnamurty H. G. (1989) Magn. Res. Chem.27: 635

    Google Scholar 

  5. Mishra A. K., Haribal M. M., Sabata B. K. (1985) Phytochemistry24: 2463

    Google Scholar 

  6. Methaji M., Pattabhi V., Krishnamurty H. G., Talukdar A. C. (1990) Acta Cryst.C 46

  7. Nagai M., Kubo M., Fujita M., Inoue T., Matsuo M. (1976) J. Chem. Comm.: 338

  8. Malterud E. E., Anthonsen T., Hjortas J. (1976) Tetrahedron Letters35: 3069

    Google Scholar 

  9. Gilmore Ch., Bryan R. F., Kupchan S. M. (1976) J. Am. Chem. Soc.98: 1947

    Google Scholar 

  10. Elix J. A., Engkaninan U., Jones A. J., Raston C. L., Sargent M. V., White A. H. (1977) Aust. J. Chem.31: 2057

    Google Scholar 

  11. Guilhem J., Bick I. R. C. (1981) J. Chem. Soc. Chem. Comm.: 1007

  12. Asakawa Y., Toyota M., Taira Z., Takemoto T. (1983) J. Org. Chem.48: 2164

    Google Scholar 

  13. Kazlauskas R., Lidgard R. O., Murphy P. T., Wells R. J., Blount J. F. (1981) Aust. J. Chem.34: 765

    Google Scholar 

  14. Leeson P. D., Ellis D., Emmett J. C., Shah V. P., Showell G. A. (1988) J. Med. Chem.31: 37

    Google Scholar 

  15. Skelton N., Williams D. H., Rance M. J., Ruddock J. C. (1990) J. Chem. Soc. Perkin Trans.I: 77

    Google Scholar 

  16. Waltho J. P., Williams D. H., Stone D. J. M., Skelton N. J. (1988) J. Amer. Chem. Soc.110: 5638

    Google Scholar 

  17. Komaromi I., Somogyi A., Dinya Z., Bognar R., Sztaricskai F. (1989) J. Mol. Struct. (Theochem.)201: 351

    Google Scholar 

  18. Williams D. H. (1984) Acc. Chem. Res.17: 364

    Google Scholar 

  19. Malabarba A., Trani A., Strazzolini P., Cietto G., Ferrari P., Tarzia G., Pallanza R., Berti M. (1989) J. Med. Chem.32: 2450

    Google Scholar 

  20. Waltho J. P., Williams D. H. (1989) J. Am. Chem. Soc.111: 2475

    Google Scholar 

  21. Jolad S. D., Hoffmann J. J., Torrance S. J., Wiedhopf R. M., Cole J. R., Arora S. K., Bates R. B., Gargiulo R. L., Kriek G. R. (1977) J. Am. Chem. Soc.99: 8040

    Google Scholar 

  22. Schmidt U., Weller D., Holder A., Lieberknecht A. (1988) Tetrahedron Letters29: 3227

    Google Scholar 

  23. Nishiyama S., Suzuki Y., Yamamura S. (1988) Tetrahedron Letters29: 559

    Google Scholar 

  24. Evans D. A., Ellman J. A., (1989) J. Am. Chem. Soc.111: 1063

    Google Scholar 

  25. Sprague J. T., Tai J. C., Yuh Y., Allinger N. L. (1987) J. Comp. Chem.8: 581

    Google Scholar 

  26. Beyer A., Wolschann P., Becker A., Buchbauer B. (1989) J. Mol. Struct.196: 371

    Google Scholar 

  27. Tripos Associates Inc., St. Louis, USA

  28. Biosym Technol., San Diego, USA

  29. Mackay D. H. J., Cross A. J., Hagler A. T. (1989) in: Fasman G. D. (ed.) Prediction of Protein Structure and the Principles of Protein Conformation. Plenum Press, New York

    Google Scholar 

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Beyer, A., Kalchhauser, H. & Wolschann, P. Molecular modeling on garuganin-I. Monatsh Chem 123, 417–423 (1992). https://doi.org/10.1007/BF00817597

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  • DOI: https://doi.org/10.1007/BF00817597

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