Studies on phosphonic acid antibiotics. III. Structure and synthesis of 3-(N-acetyl-N-hydroxyamino)propylphosphonic acid (FR-900098) and 3-(N-acetyl-N-hydroxyamino)-2(R)-hydroxypropylphosphonic acid (FR-33289)

The structures of the antibiotics FR-900098 and FR-33289, isolated from Streptomyces rubellomurius , have been established as 3-(N-acetyl-N-hydroxyamino)propylphosphonic acid and 3-(N-acetyl-N-hydroxyamino)-2(R)-hydroxypropylphosphonic acid, respectively, on the basis of spectroscopic and chemical evidence and, finally, by synthesis.