Total and Chemoenzymatic Synthesis of Seongsanamide E.

The total and chemoenzymatic synthesis of the depsipeptide natural product seongsanamide E, 3 , is described. The synthetic C-terminal N -acetylcysteamine thioester of linear natural product 1 was macrolactonized by the excised recombinant purified seongsanamide thioesterase (Sgd-TE) domain, generating 3 . Sgd-TE also effects the ring opening of 3 . Chemical synthesis provided 3 through a macrolactamization strategy. This work confirms the biosynthesis of 3 and demonstrates the power of Sgd-TE as a biocatalyst.