61 γ-Aminobutyrate Aminotransferase Inhibitor : Gabaculineの構造と合成

概要

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In the course of the studies on enzymic inhibitors of microbial origin, gabaculine, an inhibitor of γ-aminobutyrate aminotransferase, was isolated from a culture filtrate of Streptomyces toyocaensis subsp. 1093. Gabaculine, [α]_D-454°, is a novel amino acid having the formula C_7H_9O_2N. The structure was determined as 5-amino-cyclohexa-1,3-dienyl carboxylic acid on the basis of analysis of the spectral data. The synthesis, starting from cyclohexa-1,4-dienyl carboxylic acid (10), was achieved as follows: Electrophilic addition of iodoisocyanate to the olefinic double bond of 10 yielded two isomeric compounds, which were derived to the carbamates. Dehydrohalogenation of the two isomeric mixtures with DABCO afforded only a desired cyclohexa-1,3-dienyl derivative. Removal of the protective groups gave racemic gabaculine, which was identified with the natural specimen.
天然有機化合物討論会の論文
1975-10-01