Rhizocticins — New phosphono‐oligopeptides with antifungal activity

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Abstract
The widely used and well‐known bacterial strain Bacillus subtilis ATCC 6633 was found to produce two novel, antifungal hydrophilic peptide antibiotics, L‐arginyl‐L‐2‐amino‐5‐phosphono‐3‐cis‐pentenoic acid (L‐Arg‐L‐APPA, rhizocticin A) and L‐valyl‐L‐arginyl‐L‐2‐amino‐5‐phosphono‐3‐cis‐pentenoic acid (L‐Val‐L‐Arg‐L‐APPA, rhizocticin B). Besides rhizocticin A and B, the main components, small amounts of related tripeptides were detected. Instead of the L‐Val of rhizocticin B they contain L‐Ile or L‐Leu and are referred to as rhizocticins C and D, respectively. The C‐terminal residue was identified by NMR spectroscopy as the unsaturated phosphono amino acid L‐APPA, known till now only as D enantiomer. Enzymatic cleavages of rhizocticin B yielded both L‐APPA and rhizocticin A.