1961 年 81 巻 7 号 p. 938-942
The two isomers of monoglucose aspartate, i.e. 6-O-(L-α-aspartyl)-D-glucose and 6-O-(L-β-aspartyl)-D-glucose, were synthesized and their properties were examined. In both cases, 1, 2:3, 5-O-dibenzylidene-D-glucofuranose was used as the glucose moiety. For the α-ester, this was condensed with α benzyl N-benzyloxycarbonyl-L-aspartate in dicyclohexylcarbodiimide and its product was hydrogenolyzed. For the β-ester, the glucofuranose was reacted with 1-benzyl N-benzyloxycarbonyl-L-aspartate 4-chloride and the product was hydrogenolyzed.
Both of these esters were far more stable than the lysine glucose or glycine ester and did not undergo hydrolysis in aqueous solution. However, the esters were easily hydrolyzed in alkaline solution and 50% decomposition in 0.001M solution at pH 10, at 40°, was less than 5 minutes.