Studies in the biochemistry of micro-organisms. 113. Pencolide, a nitrogen-containing metabolite of Penicillium multicolor Grigorieva-Manilova and Poradielova

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Abstract
A new N-containing product, pencolide, has been obtained from the culture fluid of a strain of P. multicolor grown on Raulin-Thom medium. Pencolide, C9H9NO4, m.p. 135.5, titrates to a fugitive end point as monobasic acid and to a permanent end point as dibasic acid. It yields no acetyl derivative, but with diazomethane affords a product, C11H13 N3O4, with 1 methoxyl group, also a p-nitrobenzyl derivative. The products of alkaline hydrolysis are ammonia, a-oxobutyric acid, itaconic acid, mesaconic acid and probably citraconic acid. Oxidation with permanganate gave pyruvamide and oxamic acid. Ozonolysis afforded oxalic acid and acetic acid, acetaldehyde and ammonium oxa-late. Based on these facts, and on ultraviolet, infrared and nuclear -magnetic-resonance spectral data, the most probable structure for pencolide is 2-citraconimidobut-2-enoic-acid.