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Peptide sweeteners. 8. Synthesis and structure-taste relationship studies of L-aspartyl-D-alanyl tripeptides.
J Med Chem ; 28(10): 1527-9, 1985 Oct.
Article em En | MEDLINE | ID: mdl-4045926
Several L-aspartyl-D-alanyl tripeptides have been synthesized to investigate the structural requirements of the C-terminal amino acid needed to elicit a taste response. Following our suggestion that a rigid, hydrophobic residue is required, both alpha, alpha-dialkane and cycloalkane alpha-amino acid methyl esters were incorporated into the tripeptide. The L-aspartyl-D-alanine-based tripeptide derivatives of alpha-aminoisobutyric acid methyl ester, alpha, alpha-diethylglycine methyl ester, and alpha-aminocycloalkanecarboxylic acid methyl esters from three- to six-membered rings are sweet. The higher analogues of the cycloalkane series containing alpha-aminocycloheptanecarboxylic acid methyl ester and alpha-aminocyclooctanecarboxylic acid methyl ester are bitter. It is important to note that this series of tripeptides (analogous to the previously reported dipeptides) goes from sweet to bitter to tasteless as the ring size of the C-terminal amino acid increases. The relationships between effective volume of the C-terminal residue, size requirements of the sweet receptor, and taste are discussed.
Assuntos
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Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Oligopeptídeos / Edulcorantes / Paladar Idioma: En Revista: J Med Chem Assunto da revista: QUIMICA Ano de publicação: 1985 Tipo de documento: Article
Buscar no Google
Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Oligopeptídeos / Edulcorantes / Paladar Idioma: En Revista: J Med Chem Assunto da revista: QUIMICA Ano de publicação: 1985 Tipo de documento: Article