Structure 1 has been established for roridin E (Cz9Ha808), an antibiotic isolated from cultures of Myrothecium species. Base catalysed hydrolysis of 1 gave the known sesquiterpene alcohol verrucarol (4; C,,H,,O,) and 2'-anhydrororidinic acid (6 ; C,,H,O,), a new dicarboxylic acid. The structure of
Über die Biosynthese des Antibioticums Verrucarin E. Verrucarine und Roridine, 19. Mitteilung [1]
✍ Scribed by P. Pfäffli; Ch. Tamm
- Publisher
- John Wiley and Sons
- Year
- 1969
- Tongue
- German
- Weight
- 578 KB
- Volume
- 52
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
The incorporation of nine 14C-labelled, assumed biosynthetic precursors of verrucarin E (1) formed by Myrothecium verrucaria have been measured. The antibiotic and 3-acetyl-4methyl-pyrrolc (3) derived from it wcre oxiclized, and the radioactivity of four of thc seven Catoms determined. It has been found that the carbon skeleton of vcrrucarin E does not originate from proline, glutamic acid and its biogentic equivalcnts nor from 5-amino-levulinic acid, but is built up from four acetate units with loss of one carboxyl C-atom. These results are rationalized by proposing a biogenetic pathway for verrucarin E.
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