Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Structure–Taste Relationships of Aspartyl Tetrapeptide Esters
Yasuo Ariyoshi
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1985 Volume 58 Issue 6 Pages 1727-1730

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Abstract

A series of fourteen analogues of L-α-Asp–Gly–Gly–Gly–OMe has been synthesized in relation to structural features of sweet peptides. The rule in the structure-taste relationships of tripeptides barely applies to the aspartyl tetrapeptide esters. In order for the aspartyl tetrapeptide esters to be sweet, the second amino acid must have a D-configuration and a small, compact alkyl side chain. However, the sweetness was accompanied by a bitter or astringent taste. Moreover, some of the tetrapeptides were not sweet but bitter, though they satisfied the requirements for sweet peptides. With increasing length of a peptide, it becomes difficult to fit the deep receptor pocket.

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