Comparison of taste qualities and thresholds of D- and L-amino acids

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Abstract

The traditional generalization concerning the influence of chirality on the taste of amino acids, i.e. that L-forms are bitter or tasteless and D-forms are sweet, must be amended on the basis of the data presented here. For example, some enantiomer pairs such as L- and D-serine and L- and D-alanine exhibit similar sweet qualities. Other enantiomer pairs taste quite different from one another, such as L-proline which has a sweet component and D-proline which is bitter. The rank order of the threshold values for the D-forms tends to parallel those for the L-forms; the rank order correlation (Spearman's rho) is 0.87. However, several statistically significant threshold changes were found. Two amino acids with aromatic side chains, tryptophan and phenylalanine, have greatly reduced thresholds in the D-form while asparagine and aspartic acid, along with proline, have considerably higher thresholds in the D-form. In general, it was found that whenever a marked taste difference exists, there is a trend toward a relatively large difference in threshold values between the enantiomers. It was not found, however, that a large difference in threshold was always accompanied by a significant quality difference, or that the particular taste quality of either of the pair was a predictor of the magnitude of the threshold ratio or of which of the two forms had the highest threshold.

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    This paper was supported in part by a grant to the senior author, NIA AG00443.

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