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https://hdl.handle.net/1822/17870
Título: | Synthesis of novel non-proteinogenic amino acids : n-ethyl-alpha, beta-dehydroamino acid methyl esters |
Autor(es): | Monteiro, Luís S. Kołomańska, Joanna Suárez, Ana C. |
Palavras-chave: | Nosylamino acids α,β-dehydroamino acids β-elimination N-alkylation Amino acids alpha,beta-Dehydroamino acids Alkylation N-Ethyl-alpha,beta-dehydroamino acids N-Ethyl-α-β-dehydroamino acids |
Data: | 2010 |
Editora: | Wiley-VCH Verlag |
Revista: | European Journal of Organic Chemistry |
Resumo(s): | Two routes for the synthesis of N-ethyl-N-(4-nitrophenylsulfonyl)-alpha,beta-dehydroamino acid derivatives from serine, threonine and phenylserine derivatives are presented. One route consists of dehydration of N-(4-nitrophenylsulfonyl)-beta-hydroxyamino acid esters with di-tert-butyl dicarbonate catalyzed by 4-(dimethylamino)pyridine, followed by alkylation of the N-(4-nitrophenylsulfonyl)-alpha,beta-dehydroamino acid methyl esters obtained with triethyloxonium tetrafluoroborate. The second strategy applied the same procedures but in inverse order: alkylation followed by dehydration. These methods made it possible to obtain for the first time, new non-natural amino acids, which incorporate both an N-ethyl and an alpha,beta-dehydro moiety. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/17870 |
DOI: | 10.1002/ejoc.201001302 |
ISSN: | 1434-193X |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2010-Eur. J. Org. Chem.pdf | 227,8 kB | Adobe PDF | Ver/Abrir |