81(P10) 醤油オリ生成促成因子 : 合成と活性(ポスター発表の部)

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Soy sauce is one of the traditional fermented seasonings used in Japan. Raw soy sauce (filtrate of the fermented mash) is pasteurized at a temperature of 70 to 85℃, and stored in a tank, in order to stop the microbial and enzymatic reaction and to stabilize the flavor and color, respectively. During this treatment, a sediment gradually formed. Promotor of sediment formation at 60℃ wsa first isolated and purified from raw soy sauce by heating. The structure of promotor was identified as L-glutamic acid 5-n-butyl ester(1a, R=n-Bu). Using L-glutamic acid 5-n-butyl ester (1a) as a leading compound, we synthesized L-glutamic acid 5-alkyl ester(1) and L-glutamic acid 1-alkyl ester(1') to search for a more active compound and to study the structure-activity analyses. The sediment is mainly composed of protein. It does not however follow the heat-denaturation curve of protein. Denaturation is rapid and pronounced around 60℃, but not around 85℃, and is less pronounced between 70 and 80℃. We found that the low-molecular-weight fraction (less than 500) of raw soy sauce contained a promotor of sediment formation at temperatures around 60℃, and an inhibitor of sediment formation at temperature of around 70 to 85℃. The isolation and purification of the promotor of sediment formation by means of extraction with organic solvents, gel filtration, and HPLC from raw soy sauce. An identification of the promoter was attempted. Generally esters (1 and 1') were synthesized from L-glutamic acid and alcohol by using mineral acid. But this method gave low yield and no selectivity. So we planned a new synthetic method using two different benzyl reagents for synthesis of two types of esters. In the case of ester(1), benzyl halide was used. Otherwise in the case of ester(1'), benzyl alcohol was used. By this method we achieved selective sythesis of each four type esters(1) and (1') in relative high yields. Now sediment-forming activity of these esters(1) and (1') is being examined.
天然有機化合物討論会の論文
1999-09-01

81(P10) 醤油オリ生成促成因子 : 合成と活性(ポスター発表の部)

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