Diethyl glutomateよりPyrrolidonoylamideの生成に関する研究

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It has been found that pyrrolidonecarboxylamide is easily obtained as much as 64% of the theoretical amount by the following simple procedure. Diethyl glutamate is dissolved in 27% ammoniacal aqueous solution, and it is evaporated to small bulk on a water bath after standing for several days at room temperature. The substance, precipitated from the condensed solution by leaving it or by adding alcohol to it, is recrystallized from alcohol. And also, it has been recognized that pyrrolidonecarboxylamide can be yielded from diethylglutamate by the same method as the preparation of 2, 5-diketopiperazine-3; 6-diacetyl diamide from diethyl aspartate while 2, 5-diketopiperazine-3, 6-dipropion diamide can not be produced from diethyl glutamate by the same method. The following facts seem to be true from the above experiments with reference to the reports of the studies carried out by other chemists. 1. The pyrrolidonoyl peptide such as eisenin isolated formerly from Eisenia bicyclis by the author may be transformed from glutaminyl peptide having a free amino group at the α car-bon atom and a acid-amide group at the γ carbon atom in the glutamic acid residue, during the treatment of isolation of the peptide or by a certain biological action in the natural living tissue. 2. It is depending on the preferred positions of the carbonyl group (not at the α carbonatom) and the amino group (at the α carbon atom) in the configuration of the amino acid molecule which is characterized by highly restricted free rotation about the simple carbon-car-bon bond caused by the traction of these functional -groups, that the pyrrolidone ring is easily formed, but the diketopiperazine ring is not formed, from diester or diamide of glutamic acid, while the diketopiperazine ring is formed from the same derivatives of aspartic acid.
社団法人日本農芸化学会の論文

Diethyl glutomateよりPyrrolidonoylamideの生成に関する研究

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