Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst

Detalhes bibliográficos
Autor(a) principal: Sousa, Ana Catarina
Data de Publicação: 2020
Outros Autores: Santos, Iolanda, Piedade, M. Fatima M., Martins, Lígia O., Robalo, M. Paula
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10400.21/11883
Resumo: An efficient and environmentally benign biocatalytic strategy for the synthesis of substituted 4-arylamino-1,2-naphthoquinones was developed, through a cross-coupling reaction in which the 1,2-naphthoquinone nucleus, formed in the biocatalytic process mediated by CotA-laccase from Bacillus subtilis, is the key synthetic intermediate. Electrochemical data and kinetic parameters were determined revealing a significant higher specificity of CotA-laccase for 4-amino-3-hydroxynaphthalene-1-sulfonic acid (AHNSA). This ability of CotA-laccase to discriminate between oxidisable aromatic amines allows the set-up of one-pot reactions in the presence of the enzyme, between AHNSA and a set of appropriate aromatic amines under mild reaction conditions.
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spelling Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as BiocatalystCotA-laccase4-arylamino-12-naphthoquinonesBiocatalysisGreen synthesisAn efficient and environmentally benign biocatalytic strategy for the synthesis of substituted 4-arylamino-1,2-naphthoquinones was developed, through a cross-coupling reaction in which the 1,2-naphthoquinone nucleus, formed in the biocatalytic process mediated by CotA-laccase from Bacillus subtilis, is the key synthetic intermediate. Electrochemical data and kinetic parameters were determined revealing a significant higher specificity of CotA-laccase for 4-amino-3-hydroxynaphthalene-1-sulfonic acid (AHNSA). This ability of CotA-laccase to discriminate between oxidisable aromatic amines allows the set-up of one-pot reactions in the presence of the enzyme, between AHNSA and a set of appropriate aromatic amines under mild reaction conditions.Wiley-VCH VerlagRCIPLSousa, Ana CatarinaSantos, IolandaPiedade, M. Fatima M.Martins, Lígia O.Robalo, M. Paula2020-06-18T14:30:14Z2020-08-192020-08-19T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.21/11883engSOUSA, Ana Catarina; [et al] – Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst. Advanced Synthesis and Catalysis. ISSN 1615-4169. Vol. 362, N.º 16 (2020), pp. 3380-33871615-416910.1002/adsc.202000082metadata only accessinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-08-03T10:03:43Zoai:repositorio.ipl.pt:10400.21/11883Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:20:04.822748Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst
title Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst
spellingShingle Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst
Sousa, Ana Catarina
CotA-laccase
4-arylamino-1
2-naphthoquinones
Biocatalysis
Green synthesis
title_short Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst
title_full Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst
title_fullStr Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst
title_full_unstemmed Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst
title_sort Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst
author Sousa, Ana Catarina
author_facet Sousa, Ana Catarina
Santos, Iolanda
Piedade, M. Fatima M.
Martins, Lígia O.
Robalo, M. Paula
author_role author
author2 Santos, Iolanda
Piedade, M. Fatima M.
Martins, Lígia O.
Robalo, M. Paula
author2_role author
author
author
author
dc.contributor.none.fl_str_mv RCIPL
dc.contributor.author.fl_str_mv Sousa, Ana Catarina
Santos, Iolanda
Piedade, M. Fatima M.
Martins, Lígia O.
Robalo, M. Paula
dc.subject.por.fl_str_mv CotA-laccase
4-arylamino-1
2-naphthoquinones
Biocatalysis
Green synthesis
topic CotA-laccase
4-arylamino-1
2-naphthoquinones
Biocatalysis
Green synthesis
description An efficient and environmentally benign biocatalytic strategy for the synthesis of substituted 4-arylamino-1,2-naphthoquinones was developed, through a cross-coupling reaction in which the 1,2-naphthoquinone nucleus, formed in the biocatalytic process mediated by CotA-laccase from Bacillus subtilis, is the key synthetic intermediate. Electrochemical data and kinetic parameters were determined revealing a significant higher specificity of CotA-laccase for 4-amino-3-hydroxynaphthalene-1-sulfonic acid (AHNSA). This ability of CotA-laccase to discriminate between oxidisable aromatic amines allows the set-up of one-pot reactions in the presence of the enzyme, between AHNSA and a set of appropriate aromatic amines under mild reaction conditions.
publishDate 2020
dc.date.none.fl_str_mv 2020-06-18T14:30:14Z
2020-08-19
2020-08-19T00:00:00Z
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 http://hdl.handle.net/10400.21/11883
url http://hdl.handle.net/10400.21/11883
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv SOUSA, Ana Catarina; [et al] – Synthesis of Substituted 4-Arylamine-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst. Advanced Synthesis and Catalysis. ISSN 1615-4169. Vol. 362, N.º 16 (2020), pp. 3380-3387
1615-4169
10.1002/adsc.202000082
dc.rights.driver.fl_str_mv metadata only access
info:eu-repo/semantics/openAccess
rights_invalid_str_mv metadata only access
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH Verlag
publisher.none.fl_str_mv Wiley-VCH Verlag
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
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