Synthesis of non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivatives
Autor(a) principal: | |
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Data de Publicação: | 2003 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/1822/72922 |
Resumo: | Carbon nucleophiles, amines, and oxygen nucleophiles were treated with the methyl ester of N-(tert-butoxycarbonyl)-N-(p-tolylsulfonyl)-alpha,beta-didehydroalanine, and also with the methyl esters of N-(tert-butoxycarbonyl)-O-(p-tolylsulfinyl)-alpha,beta-didehydroserine and N-(tert-butoxycarbonyl)-beta-(1,2,4-triazol-1-yl)-alpha,beta-didehydroalanine, both of which were obtained from the former substrate. Carbon nucleophiles of the beta-dicarbonyl type gave furanic amino acids, which were converted into the corresponding pyrrole derivatives (dehydroprolines) in high yields, while use of amines allowed the synthesis of alpha,alpha-diamino acids and beta-amino-alpha,beta-didehydroamino acids. Different types of alkoxyamino acids were obtained by treatment of the above substrates with oxygen nucleophiles. The reactivities of the alpha,beta-didehydroaminobutyric and alpha,beta-didehydrophenylalanine analogues were also tested. Some of the methods developed were applied to the synthesis of cross-linked amino acids, namely didehydrolanthionine and histidino-alpha,beta-didehydroalanine derivatives. |
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Synthesis of non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivativesAmino acidsSynthesis designNitrogen heterocyclesalpha,beta-didehydroamino acidsDihydrofuransα,β-Didehydroamino acidsScience & TechnologyCarbon nucleophiles, amines, and oxygen nucleophiles were treated with the methyl ester of N-(tert-butoxycarbonyl)-N-(p-tolylsulfonyl)-alpha,beta-didehydroalanine, and also with the methyl esters of N-(tert-butoxycarbonyl)-O-(p-tolylsulfinyl)-alpha,beta-didehydroserine and N-(tert-butoxycarbonyl)-beta-(1,2,4-triazol-1-yl)-alpha,beta-didehydroalanine, both of which were obtained from the former substrate. Carbon nucleophiles of the beta-dicarbonyl type gave furanic amino acids, which were converted into the corresponding pyrrole derivatives (dehydroprolines) in high yields, while use of amines allowed the synthesis of alpha,alpha-diamino acids and beta-amino-alpha,beta-didehydroamino acids. Different types of alkoxyamino acids were obtained by treatment of the above substrates with oxygen nucleophiles. The reactivities of the alpha,beta-didehydroaminobutyric and alpha,beta-didehydrophenylalanine analogues were also tested. Some of the methods developed were applied to the synthesis of cross-linked amino acids, namely didehydrolanthionine and histidino-alpha,beta-didehydroalanine derivatives.Wiley-VCH VerlagUniversidade do MinhoFerreira, Paula M. T.Maia, Hernâni Lopes SilvaMonteiro, Luís S.2003-072003-07-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/72922eng1434-193X10.1002/ejoc.200300103https://doi.org/10.1002/ejoc.200300103info: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:RCAAP2023-07-21T12:22:55Zoai:repositorium.sdum.uminho.pt:1822/72922Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:16:31.556259Repositório 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 non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivatives |
title |
Synthesis of non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivatives |
spellingShingle |
Synthesis of non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivatives Ferreira, Paula M. T. Amino acids Synthesis design Nitrogen heterocycles alpha,beta-didehydroamino acids Dihydrofurans α,β-Didehydroamino acids Science & Technology |
title_short |
Synthesis of non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivatives |
title_full |
Synthesis of non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivatives |
title_fullStr |
Synthesis of non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivatives |
title_full_unstemmed |
Synthesis of non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivatives |
title_sort |
Synthesis of non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivatives |
author |
Ferreira, Paula M. T. |
author_facet |
Ferreira, Paula M. T. Maia, Hernâni Lopes Silva Monteiro, Luís S. |
author_role |
author |
author2 |
Maia, Hernâni Lopes Silva Monteiro, Luís S. |
author2_role |
author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Ferreira, Paula M. T. Maia, Hernâni Lopes Silva Monteiro, Luís S. |
dc.subject.por.fl_str_mv |
Amino acids Synthesis design Nitrogen heterocycles alpha,beta-didehydroamino acids Dihydrofurans α,β-Didehydroamino acids Science & Technology |
topic |
Amino acids Synthesis design Nitrogen heterocycles alpha,beta-didehydroamino acids Dihydrofurans α,β-Didehydroamino acids Science & Technology |
description |
Carbon nucleophiles, amines, and oxygen nucleophiles were treated with the methyl ester of N-(tert-butoxycarbonyl)-N-(p-tolylsulfonyl)-alpha,beta-didehydroalanine, and also with the methyl esters of N-(tert-butoxycarbonyl)-O-(p-tolylsulfinyl)-alpha,beta-didehydroserine and N-(tert-butoxycarbonyl)-beta-(1,2,4-triazol-1-yl)-alpha,beta-didehydroalanine, both of which were obtained from the former substrate. Carbon nucleophiles of the beta-dicarbonyl type gave furanic amino acids, which were converted into the corresponding pyrrole derivatives (dehydroprolines) in high yields, while use of amines allowed the synthesis of alpha,alpha-diamino acids and beta-amino-alpha,beta-didehydroamino acids. Different types of alkoxyamino acids were obtained by treatment of the above substrates with oxygen nucleophiles. The reactivities of the alpha,beta-didehydroaminobutyric and alpha,beta-didehydrophenylalanine analogues were also tested. Some of the methods developed were applied to the synthesis of cross-linked amino acids, namely didehydrolanthionine and histidino-alpha,beta-didehydroalanine derivatives. |
publishDate |
2003 |
dc.date.none.fl_str_mv |
2003-07 2003-07-01T00:00:00Z |
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/1822/72922 |
url |
http://hdl.handle.net/1822/72922 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
1434-193X 10.1002/ejoc.200300103 https://doi.org/10.1002/ejoc.200300103 |
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-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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1799132614640009216 |