The chemistry of unusual macrolides, 2. Spectroscopic and biosynthetic investigations of the V-type ATPase inhibitor concanamycin A

✍ Scribed by Bindseil, Kai U. ;Zeeck, Axel

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 769 KB
• Volume: 1994
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199419940313

✦ Synopsis

Abstract

The ^1^H‐ and ^13^C‐NMR spectra of the conformationally flexible macrolide concanamycin A (1) have been assigned by the use of 2D NMR techniques at low temperatures and have enabled biosynthetic studies on this most potent inhibitor of vacuolar ATPases. By feeding of different [^13^C]‐labeled precursors to Streptomyces sp. (strain Gö 22/15) the polyketide origin of the concanamycin skeleton was proved. It arises from a tetradecaketide, which is based on four acetate and seven propionate units besides one butyrate and two unusual C~2~ building blocks from the triose pool. In combination with former findings it is possible to predict the biogenetic assembly of several strongly related unusual macrolides, for which the group name “plecomacrolides” should be used in future. The results are discussed in the light of modern hypothesis as stated for polyketide pathways. magnified image