Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl

• Authors: Maria Alvarez , Edgardo Saavedra , Mónica Olivella , Fernando Suvire , Miguel Zamora , Ricardo Enriz
• Languages of publication: EN

Abstracts

EN

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

EN

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

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2012
• Volume: 10
• Issue: 1
• Pages: 248-255

Dates

published

1 - 2 - 2012

online

24 - 11 - 2011

Contributors

author

Maria Alvarez

• National University of San Luis

author

Edgardo Saavedra

• National University of the Patagonia San Juan Bosco

author

Mónica Olivella

• National University of San Luis

author

Fernando Suvire

• National University of San Luis

author

Miguel Zamora

• National University of San Luis

author

Ricardo Enriz

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Identifiers

DOI

10.2478/s11532-011-0136-1