Structural, vibrational, and electronic properties of the glucoalkaloid strictosidine: A combined experimental and theoretical study
Autor(a) principal: | |
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Data de Publicação: | 2016 |
Outros Autores: | , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional do INPA |
Texto Completo: | https://repositorio.inpa.gov.br/handle/1/15858 |
Resumo: | A detailed structural analysis and spectral behavior of the glucoalkaloid strictosidine, a precursor of all monoterpene indole alkaloids, are discussed. The experimental NMR, FTIR, and UV results were compared to the theoretical DFT spectra calculated by Becke using the three-parameter Lee-Yang-Parr (B3LYP) function with 6-31G(d) and 6-311++G(2d,p) basis sets. The theoretical geometry optimization data were compared with the X-ray data for precursors and similar structures in the associated literature. The similarity between the theoretical and experimental coupling constants values made it possible to affirm the values of dihedral angles and their configuration, reinforcing findings from previous stereochemical studies. Theoretical UV analysis agreed well with the measured experimental data, with bands assigned. Calculated HOMO/LUMO gaps show low excitation energy for strictosidine, justifying its stability and reaction kinetics. The molecular electrostatic potential map shows opposite potentials regions that form hydrogen bonds that stabilize the dimeric form, which were confirmed by excellent agreement of the dimeric form theoretical wavenumbers with the experimental IR spectrum. ESI-MS/MS data revealed patterns for the fragmentation of the protonated strictosidine molecule outlined by an NBO study. © 2016 Renyer Alves Costa et al. |
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Costa, Renyer AlvesPinheiro, Maria Lúcia BelémOliveira, Kelson Mota Teixeira deBarison, AnderssonSalomé, Kahlil SchwankaIank, Júlio RodolfoSilva, Noam Gadelha daCabral, Tiara SousaCosta, Emmanoel Vilaca?2020-05-19T19:58:41Z2020-05-19T19:58:41Z2016https://repositorio.inpa.gov.br/handle/1/1585810.1155/2016/1752429A detailed structural analysis and spectral behavior of the glucoalkaloid strictosidine, a precursor of all monoterpene indole alkaloids, are discussed. The experimental NMR, FTIR, and UV results were compared to the theoretical DFT spectra calculated by Becke using the three-parameter Lee-Yang-Parr (B3LYP) function with 6-31G(d) and 6-311++G(2d,p) basis sets. The theoretical geometry optimization data were compared with the X-ray data for precursors and similar structures in the associated literature. The similarity between the theoretical and experimental coupling constants values made it possible to affirm the values of dihedral angles and their configuration, reinforcing findings from previous stereochemical studies. Theoretical UV analysis agreed well with the measured experimental data, with bands assigned. Calculated HOMO/LUMO gaps show low excitation energy for strictosidine, justifying its stability and reaction kinetics. The molecular electrostatic potential map shows opposite potentials regions that form hydrogen bonds that stabilize the dimeric form, which were confirmed by excellent agreement of the dimeric form theoretical wavenumbers with the experimental IR spectrum. ESI-MS/MS data revealed patterns for the fragmentation of the protonated strictosidine molecule outlined by an NBO study. © 2016 Renyer Alves Costa et al.Volume 2016Attribution-NonCommercial-NoDerivs 3.0 Brazilhttp://creativecommons.org/licenses/by-nc-nd/3.0/br/info:eu-repo/semantics/openAccessStructural, vibrational, and electronic properties of the glucoalkaloid strictosidine: A combined experimental and theoretical studyinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleJournal of Chemistryengreponame:Repositório Institucional do INPAinstname:Instituto Nacional de Pesquisas da Amazônia (INPA)instacron:INPAORIGINALartigo-inpa.pdfartigo-inpa.pdfapplication/pdf3238352https://repositorio.inpa.gov.br/bitstream/1/15858/1/artigo-inpa.pdfdd3f12ddb98a6a84288d07fe34620565MD511/158582020-05-19 16:16:38.576oai:repositorio:1/15858Repositório de PublicaçõesPUBhttps://repositorio.inpa.gov.br/oai/requestopendoar:2020-05-19T20:16:38Repositório Institucional do INPA - Instituto Nacional de Pesquisas da Amazônia (INPA)false |
dc.title.en.fl_str_mv |
Structural, vibrational, and electronic properties of the glucoalkaloid strictosidine: A combined experimental and theoretical study |
title |
Structural, vibrational, and electronic properties of the glucoalkaloid strictosidine: A combined experimental and theoretical study |
spellingShingle |
Structural, vibrational, and electronic properties of the glucoalkaloid strictosidine: A combined experimental and theoretical study Costa, Renyer Alves |
title_short |
Structural, vibrational, and electronic properties of the glucoalkaloid strictosidine: A combined experimental and theoretical study |
title_full |
Structural, vibrational, and electronic properties of the glucoalkaloid strictosidine: A combined experimental and theoretical study |
title_fullStr |
Structural, vibrational, and electronic properties of the glucoalkaloid strictosidine: A combined experimental and theoretical study |
title_full_unstemmed |
Structural, vibrational, and electronic properties of the glucoalkaloid strictosidine: A combined experimental and theoretical study |
title_sort |
Structural, vibrational, and electronic properties of the glucoalkaloid strictosidine: A combined experimental and theoretical study |
author |
Costa, Renyer Alves |
author_facet |
Costa, Renyer Alves Pinheiro, Maria Lúcia Belém Oliveira, Kelson Mota Teixeira de Barison, Andersson Salomé, Kahlil Schwanka Iank, Júlio Rodolfo Silva, Noam Gadelha da Cabral, Tiara Sousa Costa, Emmanoel Vilaca? |
author_role |
author |
author2 |
Pinheiro, Maria Lúcia Belém Oliveira, Kelson Mota Teixeira de Barison, Andersson Salomé, Kahlil Schwanka Iank, Júlio Rodolfo Silva, Noam Gadelha da Cabral, Tiara Sousa Costa, Emmanoel Vilaca? |
author2_role |
author author author author author author author author |
dc.contributor.author.fl_str_mv |
Costa, Renyer Alves Pinheiro, Maria Lúcia Belém Oliveira, Kelson Mota Teixeira de Barison, Andersson Salomé, Kahlil Schwanka Iank, Júlio Rodolfo Silva, Noam Gadelha da Cabral, Tiara Sousa Costa, Emmanoel Vilaca? |
description |
A detailed structural analysis and spectral behavior of the glucoalkaloid strictosidine, a precursor of all monoterpene indole alkaloids, are discussed. The experimental NMR, FTIR, and UV results were compared to the theoretical DFT spectra calculated by Becke using the three-parameter Lee-Yang-Parr (B3LYP) function with 6-31G(d) and 6-311++G(2d,p) basis sets. The theoretical geometry optimization data were compared with the X-ray data for precursors and similar structures in the associated literature. The similarity between the theoretical and experimental coupling constants values made it possible to affirm the values of dihedral angles and their configuration, reinforcing findings from previous stereochemical studies. Theoretical UV analysis agreed well with the measured experimental data, with bands assigned. Calculated HOMO/LUMO gaps show low excitation energy for strictosidine, justifying its stability and reaction kinetics. The molecular electrostatic potential map shows opposite potentials regions that form hydrogen bonds that stabilize the dimeric form, which were confirmed by excellent agreement of the dimeric form theoretical wavenumbers with the experimental IR spectrum. ESI-MS/MS data revealed patterns for the fragmentation of the protonated strictosidine molecule outlined by an NBO study. © 2016 Renyer Alves Costa et al. |
publishDate |
2016 |
dc.date.issued.fl_str_mv |
2016 |
dc.date.accessioned.fl_str_mv |
2020-05-19T19:58:41Z |
dc.date.available.fl_str_mv |
2020-05-19T19:58:41Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://repositorio.inpa.gov.br/handle/1/15858 |
dc.identifier.doi.none.fl_str_mv |
10.1155/2016/1752429 |
url |
https://repositorio.inpa.gov.br/handle/1/15858 |
identifier_str_mv |
10.1155/2016/1752429 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.ispartof.pt_BR.fl_str_mv |
Volume 2016 |
dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nc-nd/3.0/br/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nc-nd/3.0/br/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Journal of Chemistry |
publisher.none.fl_str_mv |
Journal of Chemistry |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional do INPA instname:Instituto Nacional de Pesquisas da Amazônia (INPA) instacron:INPA |
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Instituto Nacional de Pesquisas da Amazônia (INPA) |
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INPA |
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INPA |
reponame_str |
Repositório Institucional do INPA |
collection |
Repositório Institucional do INPA |
bitstream.url.fl_str_mv |
https://repositorio.inpa.gov.br/bitstream/1/15858/1/artigo-inpa.pdf |
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Repositório Institucional do INPA - Instituto Nacional de Pesquisas da Amazônia (INPA) |
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