1007552-45-5Relevant academic research and scientific papers
Studies on umami taste. Synthesis of new guanosine 5′-phosphate derivatives and their synergistic effect with monosodium glutamate
Cairoli, Paola,Morelli, Carlo F.,Speranza, Giovanna,Manitto, Paolo,Pieraccini, Stefano,Sironi, Maurizio
experimental part, p. 1043 - 1050 (2009/05/08)
A number of N2-alkyl and N2-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 (γ values) were estimated through subjective comparisons of MSG/nucleotide mixtures in water with appropriate solutions of MSG alone. Assuming β = γ[nucleotide]/γ[IMP], β 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 α-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.
