Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/72922
Título: | Synthesis of non-natural amino acids from N-(p-tolylsulfonyl)-alpha,beta-didehydroamino acid derivatives |
Autor(es): | Ferreira, Paula M. T. Maia, Hernâni Lopes Silva Monteiro, Luís S. |
Palavras-chave: | Amino acids Synthesis design Nitrogen heterocycles alpha,beta-didehydroamino acids Dihydrofurans α,β-Didehydroamino acids |
Data: | Jul-2003 |
Editora: | Wiley-VCH Verlag |
Revista: | European Journal of Organic Chemistry |
Resumo(s): | 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. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/72922 |
DOI: | 10.1002/ejoc.200300103 |
ISSN: | 1434-193X |
Versão da editora: | https://doi.org/10.1002/ejoc.200300103 |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
---|---|---|---|---|
2003-Eur. J. Org. Chem. 2635.pdf | 177,14 kB | Adobe PDF | Ver/Abrir |