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Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl

  • Research Article
  • Published:
Central European Journal of Chemistry

Abstract

The multidimensional Conformational Potential Energy Hypersurface (PEHS) of cyclotrisarcosyl was comprehensively investigated at the DFT (B3LYP/6-31G(d), B3LYP/6-31G(d,p) and B3LYP/6-311++G(d,p)), levels of theory. The equilibrium structures, their relative stability, and the Transition State (TS) structures involved in the conformational interconversion pathways were analyzed. Aug-cc-pVTZ//B3LYP/6-311++G(d,p) and MP2/6-31G(d)//B3LYP/6-311++G(d,p) single point calculations predict a symmetric cis-cis-cis crown conformation as the energetically preferred form for this compound, which is in agreement with the experimental data. The conformational interconversion between the global minimum and the twist form requires 20.88 kcal mol-1 at the MP2/6-31G(d)//B3LYP/6-311++G(d,p) level of theory. Our results allow us to form a concise idea about the internal intricacies of the PEHSs of this cyclic tripeptide, describing the conformations as well as the conformational interconversion processes in this hypersurface. In addition, a comparative analysis between the conformational behaviors of cyclotrisarcosyl with that previously reported for cyclotriglycine was carried out

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References

  1. N. Tamilarasu, I. Huq, T. Rana, Bioorg. Med. Chem. Lett. 10(9), 971 (2000)

    Article  CAS  Google Scholar 

  2. M. Andrews, C. McInnes, G. Kontopidis, L. Innes, A. Cowan, A. Plater, P. Fischer, Org. Biomol. Chem. 2, 2735 (2004)

    Article  CAS  Google Scholar 

  3. M. Dygort, N. Go, H. Scheraga, Macromolecules 8(6), 750 (1975)

    Article  Google Scholar 

  4. F. Suvire, L. Santagata, J. Bombasaro, R. Enriz, J. Comput. Chem. 27(2), 188 (2006)

    Article  CAS  Google Scholar 

  5. M. Zamora, F. Suvire, R. Enriz, J. Comput. Chem. 29(2), 280 (2008)

    Article  CAS  Google Scholar 

  6. R. Tosso, M. Zamora, F. Suvire, R. Enriz, J. Phys. Chem. A 113(40), 10818 (2009)

    Article  CAS  Google Scholar 

  7. G. Ramachandran, V. Sasisekharan, Adven. Prot. Chem. 23, 283 (1968)

    Article  CAS  Google Scholar 

  8. L. LaPlanche, M. Rogers, J. Am. Chem. Soc. 86(3), 337 (1964)

    Article  CAS  Google Scholar 

  9. M. Perricaudet, A. Pullman, Int. J. Pept. Protein Res. 5(2), 99 (1973)

    Article  CAS  Google Scholar 

  10. D. Christensen, N. Kortzeborn, B. Bak, J. Led. J. Chem. Phys. 53, 3912 (1970)

    CAS  Google Scholar 

  11. D. Schnur, Y. Yun, D. Dalton, J. Org. Chem. 54(16), 3779 (1989)

    Article  CAS  Google Scholar 

  12. A. Radzicka, L. Pedersen, R. Wolfenden, Biochem. J. 27(12), 4538 (1988)

    Article  CAS  Google Scholar 

  13. L. Jorgensen, J. Gao, J. Am. Chem. 110(13), 4212 (1988)

    Article  CAS  Google Scholar 

  14. H. Baldoni, G. Zamarbide, R. Enriz, E. Jáuregui, O. Farkas, A. Perczel, S. Salpietro, I. Csizmadia, J. Mol. Struct. (THEOCHEM) 500, 97 (2000)

    Article  CAS  Google Scholar 

  15. P. Groth, Acta Chem. Scand. 30A, 838 (1976)

    Article  Google Scholar 

  16. J. Schaug, Acta Chem. Scand. 25(7), 2271 (1971)

    Google Scholar 

  17. J. Dale, K. Titlestad, Acta Chem. Scand. B29, 353 (1975)

    Article  CAS  Google Scholar 

  18. J. Dale, K. Titlestad, J. Chem. Soc. 12, 656 (1969)

    Google Scholar 

  19. C. Ramakrishnan, P. Paul, K. Ramnarayan, Suppl. J. Biosci. 8, 239 (1985)

    Article  CAS  Google Scholar 

  20. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision B.05, Gaussian, Inc., (Pittsburgh PA, 2003)

  21. L. Santagata, F. Suvire, R. Enriz, J. Torday, I. Csizmadia. THEOCHEM 465, 33 (1999)

    Article  Google Scholar 

  22. L. Santagata, F. Suvire, R. Enriz, THEOCHEM 507, 89 (2000)

    Article  CAS  Google Scholar 

  23. L. Santagata, F. Suvire, R. Enriz, THEOCHEM 536, 173 (2001)

    Article  CAS  Google Scholar 

  24. L. Santagata, F. Suvire, R. Enriz, THEOCHEM 571, 91 (2001)

    Article  CAS  Google Scholar 

  25. C. Gonzalez, H. Schlegel, J. Chem. Phys. 90, 2154 (1989)

    Article  CAS  Google Scholar 

  26. C. Gonzalez, H. Schlegel, J. Phys. Chem. 94, 5523 (1990)

    Article  CAS  Google Scholar 

  27. P. Mezey, Potential Energy Hypersurfaces (Elsevier, Amsterdam and New York, 1987)

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Chemistry, Biochemistry and Pharmacy, National University of San Luis, 5700, San Luis, Argentine

    Maria A. Alvarez, Mónica S. Olivella, Fernando D. Suvire, Miguel A. Zamora & Ricardo D. Enriz

  2. Faculty of Naturals Sciences, National University of the Patagonia San Juan Bosco, 9000, Chubut, Argentine

    Edgardo J. Saavedra

  3. IMIBIO-CONICET, UNSL, 5700, San Luis, Argentine

    Ricardo D. Enriz

Authors
  1. Maria A. Alvarez
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  2. Edgardo J. Saavedra
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  3. Mónica S. Olivella
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  4. Fernando D. Suvire
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  5. Miguel A. Zamora
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  6. Ricardo D. Enriz
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Correspondence to Miguel A. Zamora.

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Alvarez, M.A., Saavedra, E.J., Olivella, M.S. et al. Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl. cent.eur.j.chem. 10, 248–255 (2012). https://doi.org/10.2478/s11532-011-0136-1

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  • DOI: https://doi.org/10.2478/s11532-011-0136-1

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