56 シイタケ菌発育阻害因子,Trichopolynの構造研究

概要

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Trichopolyns A (1) and B (2) are antibiotics produced by Trichoderma polysporum (Link ex Pers.) Rifai (TMI 60146), a species of fungus causing serious damage against the cultivation of an edible mushroom, Lentinus edodes. The former (1) was found to be the nitric acid salt of a basic peptide, trichopolyn, while the latter (2) was shown to be trichopolyn hydrochloride. In addition to the partial structures, [A] and [B], proposed previously, the structures of the unknown parts, [X] and [Y], obtained by vigorous hydrolysis of 2 were elucidated to be 4-methyl-6-(2-oxobutyl)-pipecolic acid (7) and N-(2'-aminopropyl)-N-methyl-2-aminoethanol (5), respectively. Compound 5 was synthetically derived from L-alanine. All chiral amino acids were also proved to belong to L-series, except that the absolute configuration of 7 remained unsolved. A partial hydrolysis of 2 gave three fragments 9-11. Their structures were determined by mass spectrometry and chemical degradation. Thus, trichopolyn is represented as [A]-7-[B]-Aib-5-OH (see Chart 8), where [A] is N-(2-methyl-decanoyl)-proline and [B] is Ala-Aib(=α-aminoisobutyric acid)-Aib-Ile-Ala-Aib.
天然有機化合物討論会の論文
1979-09-20