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Open Chemistry

formerly Central European Journal of Chemistry

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Volume 10, Issue 1


Volume 13 (2015)

Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl

Maria Alvarez / Edgardo Saavedra / Mónica Olivella / Fernando Suvire / Miguel Zamora / Ricardo Enriz
Published Online: 2011-11-24 | DOI: https://doi.org/10.2478/s11532-011-0136-1


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

Keywords: Cyclic tripeptides; Potential energy hypersurface; Conformational study; DFT calculations; Cyclotrisarcosyl

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About the article

Published Online: 2011-11-24

Published in Print: 2012-02-01

Citation Information: Open Chemistry, Volume 10, Issue 1, Pages 248–255, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-011-0136-1.

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© 2011 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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