Discovery of Presaccharothriolide X, a Retro-Michael Reaction Product of Saccharothriolide B, from the Rare Actinomycete Saccharothrix sp. A1506.

Abstract

The highly reactive precursor molecule, presaccharothriolide X, was successfully isolated from the rare actinomycete Saccharothrix sp. A1506. The comparable biological activity of presaccharothriolide X and its Michael addition product saccharothriolide B unveils a unique masking/activating property of 2-aminophenol. Unexpectedly, 2-aminophenol in saccharothriolide B was eliminated through a retro-Michael reaction, to yield presaccharothriolide X under physiological conditions. 2-Aminophenol might be developed into a useful protecting group for bioactive small molecules with an α,β-unsaturated ketone.