The Structure-Taste Relationships of the Dipeptide Esters Composed of L-Aspartic Acid and β-Hydroxy Amino Acids
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概要
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In order to evaluate the contribution of a hydroxyl group to the degree of sweetness of aspartyl dipeptides, we have synthesized a number of α-L-aspartyl dipeptides, such as the esters of α-L-aspartyl-L-hydroxynorleucine (<B>16</B> and <B>17</B>), -<I>O</I>-acyl-L-serine (<B>18</B>–<B>21</B>), -D-serine (<B>22</B>–<B>28</B>), -D-threonine (<B>30</B>–<B>36</B>), and -D-allothreonine (<B>37</B>–<B>43</B>); their sweetness potencies were compared with those of the corresponding dipeptides without a hydroxyl group. It has been found that a hydroxyl group makes a major contribution to the sweetness of the α-L-aspartyl dipeptide esters. Trie introduction of a hydroxyl group into the L-L peptides gave compounds with reduced potency. However, no such regularity was observed in the L–D peptides; the esters of α-L-aspartyl-D-serine (<B>22</B>–<B>28</B>) and -D-threonine (<B>30</B>–<B>36</B>) were sweeter than the corresponding esters of α-L-aspartyl-D-alanine and -D-α-amino-<I>n</I>-butyric acid respectively, while the esters of α-L-aspartyl-D-allothreonine (<B>37</B>–<B>43</B>) were less sweet than the corresponding esters of α-L-aspartyl-D-α-amino-<I>n</I>-butyric acid. The enzymatic resolution of <I>N</I>-acetyl-<I>erythro</I>- and -<I>threo</I>-β-hydroxy-DL-norleucine is also described.
- 公益社団法人 日本化学会の論文
著者
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Ariyoshi Yasuo
Central Research Laboratories Ajinomoto Co. Inc
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Yasuda Naohiko
Central Research Laboratories, Ajinomoto Co., Inc.
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Yamatani Tetsuo
Central Research Laboratories, Ajinomoto Co., Inc.
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