Mild reductive cleavage of tryptophan and histidine side-chain protecting groups

Detalhes bibliográficos
Autor(a) principal: Maia, Hernâni Lopes Silva
Data de Publicação: 2001
Outros Autores: Monteiro, Luís S., Sebastião, Joana
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/72932
Resumo: The activation potentials of the p-toluenesulfonyl and benzoyl groups as determined by cyclic voltammetry when they are Linked to indole or imidazole are less negative than when these groups are linked to aliphatic amines. This makes them most suitable for side-chain protection of tryptophan and histidine, as it allows mild selective cleavage not only by controlled-potential electrolysis but also by chemical reduction using either magnesium in anhydrous methanol or mercury-activated aluminum.
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spelling Mild reductive cleavage of tryptophan and histidine side-chain protecting groupsProtecting groupsCyclic voltammetryReductionsCleavage reactionsScience & TechnologyThe activation potentials of the p-toluenesulfonyl and benzoyl groups as determined by cyclic voltammetry when they are Linked to indole or imidazole are less negative than when these groups are linked to aliphatic amines. This makes them most suitable for side-chain protection of tryptophan and histidine, as it allows mild selective cleavage not only by controlled-potential electrolysis but also by chemical reduction using either magnesium in anhydrous methanol or mercury-activated aluminum.WileyUniversidade do MinhoMaia, Hernâni Lopes SilvaMonteiro, Luís S.Sebastião, Joana2001-052001-05-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/72932eng1434-193X1099-069010.1002/1099-0690(200105)2001:10<1967::AID-EJOC1967>3.0.CO;2-Xhttps://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/1099-0690%28200105%292001%3A10%3C1967%3A%3AAID-EJOC1967%3E3.0.CO%3B2-Xinfo: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:RCAAP2023-07-21T12:00:04Zoai:repositorium.sdum.uminho.pt:1822/72932Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T18:49:53.467112Repositório 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 Mild reductive cleavage of tryptophan and histidine side-chain protecting groups
title Mild reductive cleavage of tryptophan and histidine side-chain protecting groups
spellingShingle Mild reductive cleavage of tryptophan and histidine side-chain protecting groups
Maia, Hernâni Lopes Silva
Protecting groups
Cyclic voltammetry
Reductions
Cleavage reactions
Science & Technology
title_short Mild reductive cleavage of tryptophan and histidine side-chain protecting groups
title_full Mild reductive cleavage of tryptophan and histidine side-chain protecting groups
title_fullStr Mild reductive cleavage of tryptophan and histidine side-chain protecting groups
title_full_unstemmed Mild reductive cleavage of tryptophan and histidine side-chain protecting groups
title_sort Mild reductive cleavage of tryptophan and histidine side-chain protecting groups
author Maia, Hernâni Lopes Silva
author_facet Maia, Hernâni Lopes Silva
Monteiro, Luís S.
Sebastião, Joana
author_role author
author2 Monteiro, Luís S.
Sebastião, Joana
author2_role author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Maia, Hernâni Lopes Silva
Monteiro, Luís S.
Sebastião, Joana
dc.subject.por.fl_str_mv Protecting groups
Cyclic voltammetry
Reductions
Cleavage reactions
Science & Technology
topic Protecting groups
Cyclic voltammetry
Reductions
Cleavage reactions
Science & Technology
description The activation potentials of the p-toluenesulfonyl and benzoyl groups as determined by cyclic voltammetry when they are Linked to indole or imidazole are less negative than when these groups are linked to aliphatic amines. This makes them most suitable for side-chain protection of tryptophan and histidine, as it allows mild selective cleavage not only by controlled-potential electrolysis but also by chemical reduction using either magnesium in anhydrous methanol or mercury-activated aluminum.
publishDate 2001
dc.date.none.fl_str_mv 2001-05
2001-05-01T00:00:00Z
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/1822/72932
url http://hdl.handle.net/1822/72932
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1434-193X
1099-0690
10.1002/1099-0690(200105)2001:10<1967::AID-EJOC1967>3.0.CO;2-X
https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/1099-0690%28200105%292001%3A10%3C1967%3A%3AAID-EJOC1967%3E3.0.CO%3B2-X
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
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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