Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/48100
Título: | Synthesis of Dehydrodipeptide and N-ethyl-dehydrodipeptide Derivatives with an α-Aminoisobutyric Acid Residue |
Autor(es): | Monteiro, Luís S. Pereira-Lima, Sílvia M. M. A. Pereira, Sofia |
Palavras-chave: | Alkylation dehydration dehydroamino acids dehydrodipeptide α, α-Dialkylglicines N-Alkyl-dehydrodipeptides N-Alkylamino acids Dehydrodipeptides α α-dialkylglicines |
Data: | 2014 |
Editora: | Bentham Science Publishers |
Revista: | Current Chemical Biology |
Resumo(s): | Several dipeptides with an N-benzyloxycarbonyl or an N-(tert-butyloxycarbonyl) α-aminoisobutyric acid residue and a β-hydroxyamino acid methyl ester were subjected to dehydration to form dehydrodipeptide derivatives. N-Ethylation of these dipeptides using triethyloxonium tetrafluoroborate with potassium tert-butoxide as auxiliary base led to complex mixtures that failed to render pure products. However, when the 4-nitrophenylsulfonyl protecting group was substituted for the benzyloxycarbonyl or tert-butyloxycarbonyl groups and N,N-diisopropylethylamine was substituted for potassium tert-butoxide, the dehydrodipeptide derivatives were selectively N-alkylated at the amino terminal nitrogen in fair to high yields. Alternatively, N-ethylation can be carried out prior to dehydration. Thus, through a combination of dehydration and N-ethylation procedures, it was possible to obtain dipeptides with α-aminoisobutyric acid and dehydroamino acid residues, which are N-alkylated at the amino terminal nitrogen. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/48100 |
ISSN: | 1872-3136 |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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Manuscript BSP-CCB-2014-31-revised.pdf | 468,8 kB | Adobe PDF | Ver/Abrir |