A number of N-2-alkyl and N-2-acyl derivatives of guanosine 5'-phosphate (GMP) have been synthesized and tested for their synergistic effect with monosodium L-glutamate (MSG), the prototypical substance imparting umami taste to savory-based foods. Capacities to enhance the taste intensity of MSG (gamma values) were estimated through subjective comparisons of MSG/nucleotide mixtures in water with appropriate solutions of MSG alone. Assuming beta = gamma[nucleotide]/gamma[IMP], beta values of the N-2-substituted GMPs were found in the range 1.2-5.7. Such values appear to be related to the chain length of the substituent in the 2-position of the purine nucleus and dependent on the replacement of a CH2 group with an S atom and/or with an alpha-CO group. These findings indicate that the exocyclic NHR group of the guanine moiety is actively implicated in the synergism between GMP derivatives and MSG. Theoretical calculations suggest that an anti conformation is probably assumed by ribonucleotide molecules interacting with umami receptors.
Studies on Umami Taste. Synthesis of New Guanosine 5'-Phosphate Derivatives and Their Synergistic Effect with Monosodium Glutamate / P. Cairoli, S. Pieraccini, M. Sironi, C. Morelli, G. Speranza, P.M. Manitto. - In: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. - ISSN 0021-8561. - 56:3(2008), pp. 1043-1050. [10.1021/jf072803c]
Studies on Umami Taste. Synthesis of New Guanosine 5'-Phosphate Derivatives and Their Synergistic Effect with Monosodium Glutamate
P. CairoliPrimo
;S. PieracciniSecondo
;M. Sironi;C. Morelli;G. SperanzaPenultimo
;P.M. ManittoUltimo
2008
Abstract
A number of N-2-alkyl and N-2-acyl derivatives of guanosine 5'-phosphate (GMP) have been synthesized and tested for their synergistic effect with monosodium L-glutamate (MSG), the prototypical substance imparting umami taste to savory-based foods. Capacities to enhance the taste intensity of MSG (gamma values) were estimated through subjective comparisons of MSG/nucleotide mixtures in water with appropriate solutions of MSG alone. Assuming beta = gamma[nucleotide]/gamma[IMP], beta values of the N-2-substituted GMPs were found in the range 1.2-5.7. Such values appear to be related to the chain length of the substituent in the 2-position of the purine nucleus and dependent on the replacement of a CH2 group with an S atom and/or with an alpha-CO group. These findings indicate that the exocyclic NHR group of the guanine moiety is actively implicated in the synergism between GMP derivatives and MSG. Theoretical calculations suggest that an anti conformation is probably assumed by ribonucleotide molecules interacting with umami receptors.File | Dimensione | Formato | |
---|---|---|---|
JAFC_2008_56_1043.pdf
accesso riservato
Tipologia:
Publisher's version/PDF
Dimensione
573.84 kB
Formato
Adobe PDF
|
573.84 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.