Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions
Autor(a) principal: | |
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Data de Publicação: | 2009 |
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/1822/72915 |
Resumo: | Several bis-amino acids were prepared using a bis-Suzuki coupling (compounds 4-8, 10), a sequential Michael addition and bis-Suzuki coupling (compounds 12, 13) and a Michael addition followed by a substitution reaction (compounds 18, 19). Thus, the pure stereoisomer of the methyl esters of N-(tert-butoxycarbonyl)-beta-bromodehydroaminobutyric acid and dehydrophenylalanine and of N-benzyloxycarbonyl-beta-bromodehydroaminobutyric acid were reacted with 1,4-phenylene-bis-boronic acid or 9,9-dioctyl-9H-fluorene-2,7-bis-boronic acid using modified Suzuki coupling conditions. The corresponding bis-dehydroamino acid derivatives were obtained in good to high yields maintaining the stereochemistry of the starting materials. This reaction was also applied successfully to a brominated dehydrodipeptide and 1,4-phenylene-bis-boronic acid showing that it could be used to create cross-links in peptide chains. An N,N-diacyldehydroalanine derivative was used in a sequential Michael addition and bis-Suzuki coupling giving a p-terphenyl bis-amino acid and a fluorenyl bis-amino acid in good yields. Two bis-alpha,beta-diamino acids were obtained by a Michael addition of 1,2,4-triazole to the methyl esters of N-(4-toluenesulfonyl), N-(tert-butoxycarbonyl) dehydroamino acids followed by treatment with ethylenediamine. |
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Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactionsDehydroamino acidsBis-amino acidsBis-Suzuki couplingMichael additionSubstitution reactionScience & TechnologySeveral bis-amino acids were prepared using a bis-Suzuki coupling (compounds 4-8, 10), a sequential Michael addition and bis-Suzuki coupling (compounds 12, 13) and a Michael addition followed by a substitution reaction (compounds 18, 19). Thus, the pure stereoisomer of the methyl esters of N-(tert-butoxycarbonyl)-beta-bromodehydroaminobutyric acid and dehydrophenylalanine and of N-benzyloxycarbonyl-beta-bromodehydroaminobutyric acid were reacted with 1,4-phenylene-bis-boronic acid or 9,9-dioctyl-9H-fluorene-2,7-bis-boronic acid using modified Suzuki coupling conditions. The corresponding bis-dehydroamino acid derivatives were obtained in good to high yields maintaining the stereochemistry of the starting materials. This reaction was also applied successfully to a brominated dehydrodipeptide and 1,4-phenylene-bis-boronic acid showing that it could be used to create cross-links in peptide chains. An N,N-diacyldehydroalanine derivative was used in a sequential Michael addition and bis-Suzuki coupling giving a p-terphenyl bis-amino acid and a fluorenyl bis-amino acid in good yields. Two bis-alpha,beta-diamino acids were obtained by a Michael addition of 1,2,4-triazole to the methyl esters of N-(4-toluenesulfonyl), N-(tert-butoxycarbonyl) dehydroamino acids followed by treatment with ethylenediamine.We acknowledge the Foundation for Science and Technology (FCT), Portugal and the Fundo Europeu de Desenvolvimento Regional (FEDER) for financial support through the Centro de Quimica of University of Minho and through the project POCI/QUI/59407/2004.SpringerUniversidade do MinhoFerreira, Paula M. T.Monteiro, Luís S.Queiroz, Maria João R. P.Pereira, G.20092009-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/72915engFerreira, P.M.T., Monteiro, L.S., Queiroz, MJ.R.P. et al. Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions. Amino Acids 36, 429–436 (2009). https://doi.org/10.1007/s00726-008-0095-90939-445110.1007/s00726-008-0095-918427712https://link.springer.com/article/10.1007%2Fs00726-008-0095-9info: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:RCAAP2023-07-21T12:25:24ZPortal AgregadorONG |
dc.title.none.fl_str_mv |
Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions |
title |
Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions |
spellingShingle |
Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions Ferreira, Paula M. T. Dehydroamino acids Bis-amino acids Bis-Suzuki coupling Michael addition Substitution reaction Science & Technology |
title_short |
Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions |
title_full |
Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions |
title_fullStr |
Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions |
title_full_unstemmed |
Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions |
title_sort |
Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions |
author |
Ferreira, Paula M. T. |
author_facet |
Ferreira, Paula M. T. Monteiro, Luís S. Queiroz, Maria João R. P. Pereira, G. |
author_role |
author |
author2 |
Monteiro, Luís S. Queiroz, Maria João R. P. Pereira, G. |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Ferreira, Paula M. T. Monteiro, Luís S. Queiroz, Maria João R. P. Pereira, G. |
dc.subject.por.fl_str_mv |
Dehydroamino acids Bis-amino acids Bis-Suzuki coupling Michael addition Substitution reaction Science & Technology |
topic |
Dehydroamino acids Bis-amino acids Bis-Suzuki coupling Michael addition Substitution reaction Science & Technology |
description |
Several bis-amino acids were prepared using a bis-Suzuki coupling (compounds 4-8, 10), a sequential Michael addition and bis-Suzuki coupling (compounds 12, 13) and a Michael addition followed by a substitution reaction (compounds 18, 19). Thus, the pure stereoisomer of the methyl esters of N-(tert-butoxycarbonyl)-beta-bromodehydroaminobutyric acid and dehydrophenylalanine and of N-benzyloxycarbonyl-beta-bromodehydroaminobutyric acid were reacted with 1,4-phenylene-bis-boronic acid or 9,9-dioctyl-9H-fluorene-2,7-bis-boronic acid using modified Suzuki coupling conditions. The corresponding bis-dehydroamino acid derivatives were obtained in good to high yields maintaining the stereochemistry of the starting materials. This reaction was also applied successfully to a brominated dehydrodipeptide and 1,4-phenylene-bis-boronic acid showing that it could be used to create cross-links in peptide chains. An N,N-diacyldehydroalanine derivative was used in a sequential Michael addition and bis-Suzuki coupling giving a p-terphenyl bis-amino acid and a fluorenyl bis-amino acid in good yields. Two bis-alpha,beta-diamino acids were obtained by a Michael addition of 1,2,4-triazole to the methyl esters of N-(4-toluenesulfonyl), N-(tert-butoxycarbonyl) dehydroamino acids followed by treatment with ethylenediamine. |
publishDate |
2009 |
dc.date.none.fl_str_mv |
2009 2009-01-01T00:00:00Z |
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 |
http://hdl.handle.net/1822/72915 |
url |
http://hdl.handle.net/1822/72915 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Ferreira, P.M.T., Monteiro, L.S., Queiroz, MJ.R.P. et al. Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions. Amino Acids 36, 429–436 (2009). https://doi.org/10.1007/s00726-008-0095-9 0939-4451 10.1007/s00726-008-0095-9 18427712 https://link.springer.com/article/10.1007%2Fs00726-008-0095-9 |
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 |
Springer |
publisher.none.fl_str_mv |
Springer |
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 |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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1777303753476538368 |