title: Studies on umami taste. Synthesis of new guanosine 5'-phosphate derivatives and their synergistic effect with monosodium glutamate.
abstract: 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 (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 N2-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 CH 2 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.
authors.affiliation: Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, via Venezian 21, I-20133 Milano, Italy.
authors.forename: Paola
authors.initials: P
authors.lastname: Cairoli
authors.forename: Stefano
authors.initials: S
authors.lastname: Pieraccini
authors.forename: Maurizio
authors.initials: M
authors.lastname: Sironi
authors.forename: Carlo F
authors.initials: CF
authors.lastname: Morelli
authors.forename: Giovanna
authors.initials: G
authors.lastname: Speranza
authors.forename: Paolo
authors.initials: P
authors.lastname: Manitto
mesh_terms: D000215:Acylation; D000478:Alkylation; D004357:Drug Synergism; D006150:Guanine Nucleotides / Q000008:administration & dosage* / Q000737:chemistry; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D011685:Purine Nucleotides / Q000737:chemistry; D012970:Sodium Glutamate / Q000008:administration & dosage*; D013649:Taste
chemical_list: D006150:Guanine Nucleotides; D011685:Purine Nucleotides; D012970:Sodium Glutamate