Stereoselective synthesis of amides sharing the guanosine 5'-monophosphate scaffold and Umami enhancement studies using human sensory and hT1R1/rT1R3 receptor assays.
J Agric Food Chem
; 59(16): 8875-85, 2011 Aug 24.
Article
em En
| MEDLINE
| ID: mdl-21770456
ABSTRACT
Recent studies led to the identification of umami-enhancing (S)-N(2)-(1-carboxyethyl)- and (S)-N(2)-(1-alkylamino)carbonylalkyl)guanosine 5'-monophosphates that, together with their sensorially inactive (R)-stereoisomers, were found to be formed upon Maillard-type glycation of guanosine 5'-monophosphate (5'-GMP) with 1,3-dihydroxyacetone or glyceraldehyde, respectively. As the efficiency of this Maillard-type procedure to generate the amidated derivatives is limited by the low solubility and reactivity of long-chain alkyl amines as well as by the tedious separation of the diastereomers formed, a versatile synthesis for the (R)- and (S)-configured amides of N(2)-carboxyalkylated guanosine 5'-monophosphate was developed. Sensory evaluation of a series of N(2)-(1-alkylamino)carbonylalkyl)guanosine 5'-monophosphates revealed ß-values for umami enhancement between 0.1 and 7.7 and identified a strong influence of the stereochemistry as well as the chain length of the N(2)-substituent on the umami-enhancing activity. The observed sensory impact of the (S)-configured isomers was confirmed by recording the enhancing effect of these nucleotides on the l-glutamate-induced response of the functionally expressed T1R1/T1R3 umami receptor in a cell-based assay, thus underscoring the stereospecifity of the umami taste receptor binding site.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Olfato
/
Paladar
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Guanosina Monofosfato
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Receptores Acoplados a Proteínas G
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Amidas
Limite:
Humans
Idioma:
En
Revista:
J Agric Food Chem
Ano de publicação:
2011
Tipo de documento:
Article
País de afiliação:
Alemanha