Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000801499 |
Resumo: | The assignment of absolute configuration (AC) is a crucial step in the structural characterization of natural products, especially for those subjected to biological assays. Methods such as X-ray crystallography, stereocontrolled organic synthesis, nuclear magnetic resonance (NMR), and chiroptical spectroscopies are commonly used to determine the AC of chiral natural compounds. Even with these well-established techniques, however, unambiguous stereochemical assignments of natural products remain a challenge, resulting in an increasing number of structural misassignments being reported every year. Herein, we will present the main techniques that have been used in AC reassignments of natural products over the last 10 years, along with some selected examples. Special attention will be paid to the strengths and weaknesses of each approach. With this, we expect to provide the readers with critical information to help them to choose the appropriate methods for correct AC determinations. |
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Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decadesecondary metabolitesstereochemical reassignmentstructure revisionmisassignmentThe assignment of absolute configuration (AC) is a crucial step in the structural characterization of natural products, especially for those subjected to biological assays. Methods such as X-ray crystallography, stereocontrolled organic synthesis, nuclear magnetic resonance (NMR), and chiroptical spectroscopies are commonly used to determine the AC of chiral natural compounds. Even with these well-established techniques, however, unambiguous stereochemical assignments of natural products remain a challenge, resulting in an increasing number of structural misassignments being reported every year. Herein, we will present the main techniques that have been used in AC reassignments of natural products over the last 10 years, along with some selected examples. Special attention will be paid to the strengths and weaknesses of each approach. With this, we expect to provide the readers with critical information to help them to choose the appropriate methods for correct AC determinations.Sociedade Brasileira de Química2021-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000801499Journal of the Brazilian Chemical Society v.32 n.8 2021reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20210079info:eu-repo/semantics/openAccessBatista,Andrea N. L.Angrisani,Bianca R. P.Lima,Maria Emanuelle D.Silva,Stephanie M. P. DaSchettini,Vitória H.Chagas,Higor A.Santos Jr.,Fernando M. dosBatista Jr.,João M.Valverde,Alessandra L.eng2021-07-26T00:00:00Zoai:scielo:S0103-50532021000801499Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2021-07-26T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade |
title |
Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade |
spellingShingle |
Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade Batista,Andrea N. L. secondary metabolites stereochemical reassignment structure revision misassignment |
title_short |
Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade |
title_full |
Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade |
title_fullStr |
Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade |
title_full_unstemmed |
Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade |
title_sort |
Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade |
author |
Batista,Andrea N. L. |
author_facet |
Batista,Andrea N. L. Angrisani,Bianca R. P. Lima,Maria Emanuelle D. Silva,Stephanie M. P. Da Schettini,Vitória H. Chagas,Higor A. Santos Jr.,Fernando M. dos Batista Jr.,João M. Valverde,Alessandra L. |
author_role |
author |
author2 |
Angrisani,Bianca R. P. Lima,Maria Emanuelle D. Silva,Stephanie M. P. Da Schettini,Vitória H. Chagas,Higor A. Santos Jr.,Fernando M. dos Batista Jr.,João M. Valverde,Alessandra L. |
author2_role |
author author author author author author author author |
dc.contributor.author.fl_str_mv |
Batista,Andrea N. L. Angrisani,Bianca R. P. Lima,Maria Emanuelle D. Silva,Stephanie M. P. Da Schettini,Vitória H. Chagas,Higor A. Santos Jr.,Fernando M. dos Batista Jr.,João M. Valverde,Alessandra L. |
dc.subject.por.fl_str_mv |
secondary metabolites stereochemical reassignment structure revision misassignment |
topic |
secondary metabolites stereochemical reassignment structure revision misassignment |
description |
The assignment of absolute configuration (AC) is a crucial step in the structural characterization of natural products, especially for those subjected to biological assays. Methods such as X-ray crystallography, stereocontrolled organic synthesis, nuclear magnetic resonance (NMR), and chiroptical spectroscopies are commonly used to determine the AC of chiral natural compounds. Even with these well-established techniques, however, unambiguous stereochemical assignments of natural products remain a challenge, resulting in an increasing number of structural misassignments being reported every year. Herein, we will present the main techniques that have been used in AC reassignments of natural products over the last 10 years, along with some selected examples. Special attention will be paid to the strengths and weaknesses of each approach. With this, we expect to provide the readers with critical information to help them to choose the appropriate methods for correct AC determinations. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021-08-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000801499 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000801499 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20210079 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.32 n.8 2021 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
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1750318184378925056 |