Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl

Autores
Alvarez, Maria de Los Angeles; Saavedra, Edgardo J.; Olivella, Mónica Susana; Suvire, Fernando Daniel; Zamora, Miguel Angel; Enriz, Ricardo Daniel
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
Fil: Alvarez, Maria de Los Angeles. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Saavedra, Edgardo J.. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina
Fil: Olivella, Mónica Susana. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Suvire, Fernando Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Zamora, Miguel Angel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Materia
CONFORMATIONAL STUDY
CYCLIC TRIPEPTIDES
CYCLOTRISARCOSYL
DFT CALCULATIONS
POTENTIAL ENERGY HYPERSURFACE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/139646
Acceder
id CONICETDig_19563708eb5ca44c9728d755162c45fe
oai_identifier_str oai:ri.conicet.gov.ar:11336/139646
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Theoretical study of the conformational energy hypersurface of cyclotrisarcosylAlvarez, Maria de Los AngelesSaavedra, Edgardo J.Olivella, Mónica SusanaSuvire, Fernando DanielZamora, Miguel AngelEnriz, Ricardo DanielCONFORMATIONAL STUDYCYCLIC TRIPEPTIDESCYCLOTRISARCOSYLDFT CALCULATIONSPOTENTIAL ENERGY HYPERSURFACEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The 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.Fil: Alvarez, Maria de Los Angeles. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaFil: Saavedra, Edgardo J.. Universidad Nacional de la Patagonia "San Juan Bosco"; ArgentinaFil: Olivella, Mónica Susana. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaFil: Suvire, Fernando Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaFil: Zamora, Miguel Angel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; ArgentinaVersita2012-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/139646Alvarez, Maria de Los Angeles; Saavedra, Edgardo J.; Olivella, Mónica Susana; Suvire, Fernando Daniel; Zamora, Miguel Angel; et al.; Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl; Versita; Central European Journal of Chemistry; 10; 1; 2-2012; 248-2551895-10661644-3624CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.degruyter.com/document/doi/10.2478/s11532-011-0136-1/htmlinfo:eu-repo/semantics/altIdentifier/doi/10.2478/s11532-011-0136-1info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:12:35Zoai:ri.conicet.gov.ar:11336/139646instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-10 13:12:35.397CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl
title Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl
spellingShingle Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl
Alvarez, Maria de Los Angeles
CONFORMATIONAL STUDY
CYCLIC TRIPEPTIDES
CYCLOTRISARCOSYL
DFT CALCULATIONS
POTENTIAL ENERGY HYPERSURFACE
title_short Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl
title_full Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl
title_fullStr Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl
title_full_unstemmed Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl
title_sort Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl
dc.creator.none.fl_str_mv Alvarez, Maria de Los Angeles
Saavedra, Edgardo J.
Olivella, Mónica Susana
Suvire, Fernando Daniel
Zamora, Miguel Angel
Enriz, Ricardo Daniel
author Alvarez, Maria de Los Angeles
author_facet Alvarez, Maria de Los Angeles
Saavedra, Edgardo J.
Olivella, Mónica Susana
Suvire, Fernando Daniel
Zamora, Miguel Angel
Enriz, Ricardo Daniel
author_role author
author2 Saavedra, Edgardo J.
Olivella, Mónica Susana
Suvire, Fernando Daniel
Zamora, Miguel Angel
Enriz, Ricardo Daniel
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv CONFORMATIONAL STUDY
CYCLIC TRIPEPTIDES
CYCLOTRISARCOSYL
DFT CALCULATIONS
POTENTIAL ENERGY HYPERSURFACE
topic CONFORMATIONAL STUDY
CYCLIC TRIPEPTIDES
CYCLOTRISARCOSYL
DFT CALCULATIONS
POTENTIAL ENERGY HYPERSURFACE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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.
Fil: Alvarez, Maria de Los Angeles. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Saavedra, Edgardo J.. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina
Fil: Olivella, Mónica Susana. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Suvire, Fernando Daniel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Zamora, Miguel Angel. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Departamento de Química; Argentina
description 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.
publishDate 2012
dc.date.none.fl_str_mv 2012-02
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/139646
Alvarez, Maria de Los Angeles; Saavedra, Edgardo J.; Olivella, Mónica Susana; Suvire, Fernando Daniel; Zamora, Miguel Angel; et al.; Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl; Versita; Central European Journal of Chemistry; 10; 1; 2-2012; 248-255
1895-1066
1644-3624
CONICET Digital
CONICET
url http://hdl.handle.net/11336/139646
identifier_str_mv Alvarez, Maria de Los Angeles; Saavedra, Edgardo J.; Olivella, Mónica Susana; Suvire, Fernando Daniel; Zamora, Miguel Angel; et al.; Theoretical study of the conformational energy hypersurface of cyclotrisarcosyl; Versita; Central European Journal of Chemistry; 10; 1; 2-2012; 248-255
1895-1066
1644-3624
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.degruyter.com/document/doi/10.2478/s11532-011-0136-1/html
info:eu-repo/semantics/altIdentifier/doi/10.2478/s11532-011-0136-1
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Versita
publisher.none.fl_str_mv Versita
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.993085

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