Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid

Marine organisms are an increasingly important source of novel metabolites, some of which have already inspired or become new drugs. In addition, many of these molecules show a high degree of novelty from a structural and/or pharmacological point of view. Structure determination is generally achieve...

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Autores: Domínguez, Humberto J., Crespín, Guillermo D., Santiago-Benítez, Adrián J., Gavín, José A., Norte, Manuel, Fernandez, Jose Javier, Hernández Daranas, Antonio
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2014
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/213239
Acceso en línea:http://hdl.handle.net/10261/213239
Access Level:acceso abierto
Palabra clave:Quantum mechanical calculations
Nuclear magnetic resonance
Chemical shifts
Marine toxin
Structure determination
Stereochemistry
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spelling Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic AcidDomínguez, Humberto J.Crespín, Guillermo D.Santiago-Benítez, Adrián J.Gavín, José A.Norte, ManuelFernandez, Jose JavierHernández Daranas, AntonioQuantum mechanical calculationsNuclear magnetic resonanceChemical shiftsMarine toxinStructure determinationStereochemistryMarine organisms are an increasingly important source of novel metabolites, some of which have already inspired or become new drugs. In addition, many of these molecules show a high degree of novelty from a structural and/or pharmacological point of view. Structure determination is generally achieved by the use of a variety of spectroscopic methods, among which NMR (nuclear magnetic resonance) plays a major role and determination of the stereochemical relationships within every new molecule is generally the most challenging part in structural determination. In this communication, we have chosen okadaic acid as a model compound to perform a computational chemistry study to predict 1H and 13C NMR chemical shifts. The effect of two different solvents and conformation on the ability of DFT (density functional theory) calculations to predict the correct stereoisomer has been studiedPeer reviewedMolecular Diversity Preservation InternationalMinisterio de Asuntos Económicos y Transformación Digital (España)CSIC - Instituto Español de Oceanografía (IEO)202020202014info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/213239reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttps://doi.org/10.3390/md12010176Noinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2132392026-05-22T06:33:51Z
dc.title.none.fl_str_mv Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid
title Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid
spellingShingle Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid
Domínguez, Humberto J.
Quantum mechanical calculations
Nuclear magnetic resonance
Chemical shifts
Marine toxin
Structure determination
Stereochemistry
title_short Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid
title_full Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid
title_fullStr Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid
title_full_unstemmed Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid
title_sort Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid
dc.creator.none.fl_str_mv Domínguez, Humberto J.
Crespín, Guillermo D.
Santiago-Benítez, Adrián J.
Gavín, José A.
Norte, Manuel
Fernandez, Jose Javier
Hernández Daranas, Antonio
author Domínguez, Humberto J.
author_facet Domínguez, Humberto J.
Crespín, Guillermo D.
Santiago-Benítez, Adrián J.
Gavín, José A.
Norte, Manuel
Fernandez, Jose Javier
Hernández Daranas, Antonio
author_role author
author2 Crespín, Guillermo D.
Santiago-Benítez, Adrián J.
Gavín, José A.
Norte, Manuel
Fernandez, Jose Javier
Hernández Daranas, Antonio
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Asuntos Económicos y Transformación Digital (España)
CSIC - Instituto Español de Oceanografía (IEO)
dc.subject.none.fl_str_mv Quantum mechanical calculations
Nuclear magnetic resonance
Chemical shifts
Marine toxin
Structure determination
Stereochemistry
topic Quantum mechanical calculations
Nuclear magnetic resonance
Chemical shifts
Marine toxin
Structure determination
Stereochemistry
description Marine organisms are an increasingly important source of novel metabolites, some of which have already inspired or become new drugs. In addition, many of these molecules show a high degree of novelty from a structural and/or pharmacological point of view. Structure determination is generally achieved by the use of a variety of spectroscopic methods, among which NMR (nuclear magnetic resonance) plays a major role and determination of the stereochemical relationships within every new molecule is generally the most challenging part in structural determination. In this communication, we have chosen okadaic acid as a model compound to perform a computational chemistry study to predict 1H and 13C NMR chemical shifts. The effect of two different solvents and conformation on the ability of DFT (density functional theory) calculations to predict the correct stereoisomer has been studied
publishDate 2014
dc.date.none.fl_str_mv 2014
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/213239
url http://hdl.handle.net/10261/213239
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://doi.org/10.3390/md12010176
No
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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