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The complete stereostructure of the new antibiotic Ro 22-5417 has been established as 3-[(3S,5S)-7-oxo-1-aza-4-oxabicyclo[3.2.O]hept-3-yl]-L-alanine. This result together with the synthesis of an (3R,5R)-L-analog allowed us to postulate that clavams require the R-configuration at the ring juncture for beta-lactamase inhibitory activity, while the opposite S-stereochemistry is essential for antifungal activity.

Streptomyces clavuligerus NRRL 3585, a culture which produces a variety of beta-lactam antibiotics in the penicillin, cephalosporin and clavam families, was found to produce a new beta-lactam antibiotic, Ro 22-5417. The compound, which was neither a substrate for nor inhibitor of several beta-lactamases, showed antimicrobial activity in defined minimal medium but little or no inhibitory activity in nutrient-rich medium. The activity was bacteriostatic against Bacillus species ATCC 27860 and was antagonized by D- and L-methionine, L-cystathionine, L-homocystine and O-acetyl-L-homoserine but not by L-homoserine, L-aspartate, L-cysteine or other common amino acids, vitamins and nucleosides. Our results are consistent with Ro 22-5417 acting as an inhibitor in methionine biosynthesis.