Síntese “one pot” de selenocisteína e seus derivados via mesilato da L-serina protegida

• Ano de defesa: 2009
• Autor(a) principal: Taube Junior, Paulo Sergio
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de Santa Maria; Brasil; Química; UFSM; Programa de Pós-Graduação em Química; Centro de Ciências Naturais e Exatas
• Palavras-chave em Português: Selenocisteína; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/23898

In the present work we developed a new methodology for the “one pot” synthesis of L-seleno- and telullorocysteine, L-seleno- and telullorocystine and L-seleno- and telullorolanthionine derivatives. Through a quite versatile synthetic route, it was possible to synthesize, first mesilate of protected L-serine was reacted with different reactivate species of selenium or tellurium to get chalcogeno amino acids. For the synthesis of those seleno- and tellurocysteine derivatives, initially the esterification of the amino acid was accomplished by commercially available 1 (L-serine), to afford the respective amino ester 2. Followed by protection with (Boc2O) to afford the N-Boc amino ester 3a. Furthermore treatment with mesyl chloride to obtain the chiral mesilate 4a, in good yield, through the treatment of the N-Boc amino ester 3a with mesyl chloride in the presence of a base in CH2Cl2....