Reassignment of the Structure of the Antibiotic A53868 Reveals an Unusual Amino Dehydrophosphonic Acid

✍ Scribed by John T. Whitteck; Weijuan Ni; Benjamin M. Griffin; Andrew C. Eliot; Paul M. Thomas; Neil L. Kelleher; William W. Metcalf; Wilfred A. van der Donk

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 367 KB
• Volume: 46
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200703810

✦ Synopsis

Antibiotic biosynthesis has enjoyed a renewed interest in recent years, with most efforts directed at polyketide synthases, non-ribosomal peptide synthetases, and antimicrobial peptides. [1, 2] Relatively unexplored with respect to biosynthetic pathways are phosphonate antibiotics, despite their commercial use as pharmaceuticals, herbicides, and pesticides. [3][4][5] In fact, currently the biosynthetic pathways of only three phosphonate antibiotics are known: fosfomycin, [6] bialaphos, [7] and FR900098. [8] These studies and others [9] have uncovered intriguing new biochemical transformations involved in phosphonate biosynthesis. As part of a program to provide more insights into the biogenesis of this class of compounds, we investigated A53868, the structure of which was originally reported as 1 [10] but later revised to 2 (Scheme 1). [11] We show here that the actual structure of the compound is, however, the unusual amino dehydrophosphonic acid 3.