Biosynthesis of brefeldin A. Introduction of oxygen at the C-7 position.
The biosynthetic introduction of oxygen in position 7 of brefeldin A, a structurally unique macrolide with an alicyclic ring, was studied. [4-2H]Brefeldin C was prepared efficiently from brefeldin A. A high incorporation ratio of the labeled brefeldin C into brefeldin A by Eupenicillium brefeldianum clearly indicates that the oxygen in position 7 of brefeldin A does not contribute to the cyclopentane ring formation but is introduced during the last step of brefeldin A biosynthesis.
D000935:Antifungal Agents / Q000096:biosynthesis*; D020126:Brefeldin A; D003517:Cyclopentanes / Q000096:biosynthesis*; D009682:Magnetic Resonance Spectroscopy; D010100:Oxygen / Q000378:metabolism*; D013237:Stereoisomerism
D000935:Antifungal Agents; D003517:Cyclopentanes; D020126:Brefeldin A; C042504:brefeldin C; D010100:Oxygen