Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives
Autor(a) principal: | |
---|---|
Data de Publicação: | 2001 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | https://hdl.handle.net/1822/2196 |
Resumo: | Michael additions of nitrogen heterocycles, thiols, carbon nucleophiles and amines to dehydroalanine derivatives, including a glycyldehydroalanine peptide, were performed in fair to good yields. Dehydroaminobutyric acid derivatives reacted only with the stronger nucleophiles but in considerably lower yields and often no reaction was observed with the corresponding dehydrophenylalanine derivatives. When a tosyl group was bonded to the nitrogen atom of the dehydroamino acid, in some cases the addition product underwent elimination of this group and yielded the corresponding b-substituted derivative of the a,b-dehydroamino acid. Addition of some b- dicarbonyl compounds led to formation of products to which the structure of a,a-disubstituted cyclic amino acid derivatives was assigned. |
id |
RCAP_5ff5708c86fed436c62051cd7ac01d9b |
---|---|
oai_identifier_str |
oai:repositorium.sdum.uminho.pt:1822/2196 |
network_acronym_str |
RCAP |
network_name_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository_id_str |
7160 |
spelling |
Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivativesScience & TechnologyMichael additions of nitrogen heterocycles, thiols, carbon nucleophiles and amines to dehydroalanine derivatives, including a glycyldehydroalanine peptide, were performed in fair to good yields. Dehydroaminobutyric acid derivatives reacted only with the stronger nucleophiles but in considerably lower yields and often no reaction was observed with the corresponding dehydrophenylalanine derivatives. When a tosyl group was bonded to the nitrogen atom of the dehydroamino acid, in some cases the addition product underwent elimination of this group and yielded the corresponding b-substituted derivative of the a,b-dehydroamino acid. Addition of some b- dicarbonyl compounds led to formation of products to which the structure of a,a-disubstituted cyclic amino acid derivatives was assigned.Royal Society of ChemistryUniversidade do MinhoFerreira, Paula M. T.Maia, Hernâni L. S.Monteiro, Luís S.Sacramento, Joana20012001-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/2196engFerreira, P. M. T., Maia, H. L. S., Monteiro, L. S., & Sacramento, J. (2001). Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives. [10.1039/B106487H]. Journal of the Chemical Society, Perkin Transactions 1(23), 3167-3173. doi: 10.1039/b106487h1472-778110.1039/b106487hinfo: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:RCAAP2023-12-23T01:27:47Zoai:repositorium.sdum.uminho.pt:1822/2196Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T18:50:00.589245Repositório 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 |
Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives |
title |
Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives |
spellingShingle |
Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives Ferreira, Paula M. T. Science & Technology |
title_short |
Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives |
title_full |
Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives |
title_fullStr |
Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives |
title_full_unstemmed |
Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives |
title_sort |
Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives |
author |
Ferreira, Paula M. T. |
author_facet |
Ferreira, Paula M. T. Maia, Hernâni L. S. Monteiro, Luís S. Sacramento, Joana |
author_role |
author |
author2 |
Maia, Hernâni L. S. Monteiro, Luís S. Sacramento, Joana |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Ferreira, Paula M. T. Maia, Hernâni L. S. Monteiro, Luís S. Sacramento, Joana |
dc.subject.por.fl_str_mv |
Science & Technology |
topic |
Science & Technology |
description |
Michael additions of nitrogen heterocycles, thiols, carbon nucleophiles and amines to dehydroalanine derivatives, including a glycyldehydroalanine peptide, were performed in fair to good yields. Dehydroaminobutyric acid derivatives reacted only with the stronger nucleophiles but in considerably lower yields and often no reaction was observed with the corresponding dehydrophenylalanine derivatives. When a tosyl group was bonded to the nitrogen atom of the dehydroamino acid, in some cases the addition product underwent elimination of this group and yielded the corresponding b-substituted derivative of the a,b-dehydroamino acid. Addition of some b- dicarbonyl compounds led to formation of products to which the structure of a,a-disubstituted cyclic amino acid derivatives was assigned. |
publishDate |
2001 |
dc.date.none.fl_str_mv |
2001 2001-01-01T00:00:00Z |
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 |
https://hdl.handle.net/1822/2196 |
url |
https://hdl.handle.net/1822/2196 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Ferreira, P. M. T., Maia, H. L. S., Monteiro, L. S., & Sacramento, J. (2001). Michael addition of thiols, carbon nucleophiles and amines to dehydroamino acid and dehydropeptide derivatives. [10.1039/B106487H]. Journal of the Chemical Society, Perkin Transactions 1(23), 3167-3173. doi: 10.1039/b106487h 1472-7781 10.1039/b106487h |
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 |
Royal Society of Chemistry |
publisher.none.fl_str_mv |
Royal Society of Chemistry |
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 |
|
_version_ |
1799132267043356672 |