Detalhes bibliográficos
| Resumo: | Imidazolidin-4-ones are commonly employed as skeletal modifications in bioactive oligopeptides, either as proline surrogates or for protection of the N-terminal amino acid against aminopeptidase- and endopeptidase-catalyzed hydrolysis. Imidazolidin-4-one synthesis usually involves the reaction of an α-aminoamide moiety with a ketone or an aldehyde to yield an imine, followed by intramolecular cyclization. We have unexpectedly found that imidazolidin-4-one formation is stereoselective when benzaldehydes containing o-carboxyl or o-methoxycarbonyl substituents are reacted with α-aminoamide derivatives of the antimalarial drug primaquine. A systematic computational and experimental study on the stereoselectivity of imidazolidin-4-one formation from primaquine α-aminoamides and various substituted benzaldehydes has been carried out, and they have allowed us to conclude that intramolecular hydrogen-bonds involving the CO oxygen of the o-substituent play a crucial role. |
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| Autores principais: | Ferraz, Ricardo |
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| Outros Autores: | Gomes, José R. B.; Oliveira, Eliandre de; Moreira, Rui; Gomes, Paula |
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| Assunto: | Imidazolidin-4-ones N-terminal aminoacid α-aminoamide moiety |
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| Ano: | 2007 |
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| País: | Portugal |
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| Tipo de documento: | artigo |
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| Tipo de acesso: | acesso restrito |
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| Instituição associada: | Instituto Politécnico do Porto |
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| Idioma: | inglês |
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| Origem: | Repositório Científico do Instituto Politécnico do Porto |
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