Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/72915
Título: | Synthesis of bis-amino acid derivatives by Suzuki cross-coupling, Michael addition and substitution reactions |
Autor(es): | Ferreira, Paula M. T. Monteiro, Luís S. Queiroz, Maria João R. P. Pereira, G. |
Palavras-chave: | Dehydroamino acids Bis-amino acids Bis-Suzuki coupling Michael addition Substitution reaction |
Data: | 2009 |
Editora: | Springer |
Revista: | Amino Acids |
Citação: | 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 |
Resumo(s): | 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. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/72915 |
DOI: | 10.1007/s00726-008-0095-9 |
ISSN: | 0939-4451 |
Versão da editora: | https://link.springer.com/article/10.1007%2Fs00726-008-0095-9 |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2009-Amino Acids 429.pdf | 305,81 kB | Adobe PDF | Ver/Abrir |