Publicação
Synthesis of novel non-proteinogenic amino acids : n-ethyl-alpha, beta-dehydroamino acid methyl esters
| Resumo: | 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. |
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| Autores principais: | Monteiro, Luís S. |
| Outros Autores: | Kołomańska, Joanna; Suárez, Ana C. |
| Assunto: | 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 |
| Ano: | 2010 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| Resumo: | 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. |
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