L-2-Amino-4-methoxy-£nz?zs-3-butenoic acid was isolated from a fermentation broth of Pseudomonas aeruginosa ATCC-7700. This substance inhibited the growth of Bacillus species 1283B in a chemically defined medium. The growth inhibition was reversed by a variety of amino acids. An amino acid antimetabolite which inhibited the growth of Bacillus sp. 1283B was discovered in a fermentation broth of Pseudomonas aeruginosa ATCC-7700. The compoundwas isolated from the broth by adsorption onto an anion-exchange column followed by elution with trimethylammonium bicarbonate2), a volatile buffer. The structure was determined to be L-2-amino-4-methoxy-/r£ms-3-butenoic acid, I*, by physical chemical characterization and by reduction to L-2-amino-4-methoxybutanoic acid3), Ilia, identical with a sample prepared by enzymatic resolution of the synthetic racemate4), Illb. An unexpected product, L-2-amino-butanoic acid, II, was isolated on reduction of I employing a platinum-charcoal catalyst. The title compound is the first amino acid reported to contain an enol ether group.

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L-~2-Amino-4-pentynoic acid was isolated from a streptomycete fermentation and shown to inhibit the growth of Bacillus subtilis in a chemically defined medium. This growth inhibition was reversed by L-methionine or L-leucine. Recently several laboratories2"ll) have been interested in the search for antimetabolites in fermentation broths. Such compouds are, ordinarily, not observed in conventional antibiotic screens due to the presence of reversing metabolites in the complex media commonly employed. However, by the use of chemically defined minimal media12) it is possible to detect antimetabolite activities and, by selectively supplementing the assay medium with known substances, to determine which compounds * Streptomyces sp. #8-4(HLR-599A), isolated 1966 from a garden soil of New Brunswick, N. J., kindly supplied by Prof.

A new arginine antimetabolite was isolated from the fermentation broth of a new strain of Streptomyces and identified as 2-methyl-L-arginine.A number of antimicrobially active phytogenic and microbiogenic arginine derivatives, whose activities are reversed by arginine, have been described recently.2,3,4) We now report a new member of this series, 2-methyl-L-arginine (1), produced by a new Streptomyces species designated X-11837.