Umami and taste enhancement - Umami taste of dried scallops
10 important questions on Umami and taste enhancement - Umami taste of dried scallops
Which compound in dried scallops is the taste-active compound?
What is the difference between an R- and S-enantiomer?
- R-enantiomer: methyl group points backwards, has a much higher taste activity
- S-enantiomer: methyl group points forward
Why are flavour houses interested in the use of umami-like compounds?
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Why should (R)-strombine be synthesised organically?
- is low
- extraction would be too laborious and expensive
- variable and season-dependent --> quality of the natural product is not constant
Why is the content of (R)-strombine in scallops variable and season-dependent?
How is (R)-strombine formed within the scallop?
- The oxygen of the carbonyl (second carbon) of pyruvic acid is electronegative, drawing electrons from the carbon
- The carbon has, therefore, a partial positive charge
- The electron pair from the amine will attack this partially positive carbon and form strombine.
- Within the scallop, an enzyme is responsible for this conversion, with the advantage that the reaction is stereospecific, i.e. Only the R-enantiomer is formed.
What happens if (R)-strombine is formed by organic synthesis in the same way as in the scallop?
How is (R)-strombine formed by an alternative synthetic route?
- (R)alanine was used instead of glycine, it already has a methyl side chain that is in the right conformation
- Glyoxylic acid was used instead of pyruvic acid.
When the lone pair of the amino group of (R)-alanine attacks the carbonyl of glyoxylic acid, only the R-enantiomer of strombine can be formed, as now the chirality cannot be destroyed.
What does (R)-strombine trigger?
What discourages the use of the racemic mixture?
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