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Flavour Science: Chapter 55. Discovery and Structure-Activity Studies of Maillard-Modified Guanosine 5′-Monophosphates using Human Sensory Studies and Cell-Based Taste Receptor Assays

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Activity guided fractionation of a commercially available yeast extract led to the identification of -N2-guanosine 5′-monophosphate, a nucleotide exhibiting pronounced umami taste enhancing activity. Applying model reaction systems, this compound was found to be formed upon Maillard reaction of 5′-GMP with short chained carbohydrates. Consequently, systematic studies were undertaken to better understand thermal transformation reactions of the purine ribonucleotide resulting in two structurally diverse groups of Maillard-modified 5′-GMP derivatives which were evaluated with regard to structure–activity relationships in human sensory studies. Results suggested that substitution of the nucleotide’s exocyclic amino function with small, unpolar residues has a beneficial effect on taste enhancement. In addition, selected representatives of the 5′-GMP derivatives were tested in a cell-based taste receptor assay, underlining the human sensory results.

Pages: 11

Format: Kindle Edition

Publisher: Academic Press

Release: July 29, 2013

Flavour Science: Chapter 55. Discovery and Structure-Activity Studies of Maillard-Modified Guanosine 5′-Monophosphates using Human Sensory Studies and Cell-Based Taste Receptor Assays

0/5 ( ratings)

Activity guided fractionation of a commercially available yeast extract led to the identification of -N2-guanosine 5′-monophosphate, a nucleotide exhibiting pronounced umami taste enhancing activity. Applying model reaction systems, this compound was found to be formed upon Maillard reaction of 5′-GMP with short chained carbohydrates. Consequently, systematic studies were undertaken to better understand thermal transformation reactions of the purine ribonucleotide resulting in two structurally diverse groups of Maillard-modified 5′-GMP derivatives which were evaluated with regard to structure–activity relationships in human sensory studies. Results suggested that substitution of the nucleotide’s exocyclic amino function with small, unpolar residues has a beneficial effect on taste enhancement. In addition, selected representatives of the 5′-GMP derivatives were tested in a cell-based taste receptor assay, underlining the human sensory results.

Pages: 11

Format: Kindle Edition

Publisher: Academic Press

Release: July 29, 2013

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