rhizocticin-a and 2-amino-5-phosphono-3-pentenoic-acid

Rhizocticins and Plumbemycins are natural phosphonate antibiotics produced by the bacterial strains Bacillus subtilis ATCC 6633 and Streptomyces plumbeus, respectively. Up to now, these potential threonine synthase inhibitors have only been synthesized under enzymatic catalysis. Here we report the chemical stereoselective synthesis of the non-proteinogenic (S,Z)-2-amino-5-phosphonopent-3-enoic acid [(S,Z)-APPA] and its use for the synthesis of Rhizocticin A and Plumbemycin A. In this work, (S,Z)-APPA was synthesized via the Still-Gennari olefination starting from Garner's aldehyde. The Michaelis-Arbuzov reaction was used to form the phosphorus-carbon bond. Oligopeptides were prepared using liquid phase peptide synthesis (LPPS) and were tested against selected bacteria and fungi.

Topics: 2-Amino-5-phosphonovalerate; Anti-Infective Agents; Bacillus subtilis; Carbon-Oxygen Lyases; Enzyme Inhibitors; Fungi; Gram-Negative Bacteria; Gram-Positive Bacteria; Oligopeptides; Organophosphorus Compounds; Stereoisomerism; Streptomyces

Topics: 2-Amino-5-phosphonovalerate; Amino Acids; Antifungal Agents; Bacillus subtilis; Molecular Conformation; Oligopeptides; Organophosphorus Compounds; Stereoisomerism; Streptomyces; Threonine