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Cyclodimerization of Mohangamide A by Thioesterase Domain Is Directed by Substrates.

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Mohangamide A is a pseudo-dimeric nonribosomal peptide biosynthesized along with its monomer, WS9326A, and is expected to be formed by the head-to-tail cyclodimerization of linear WS9326A and another identical peptide… Click to show full abstract

Mohangamide A is a pseudo-dimeric nonribosomal peptide biosynthesized along with its monomer, WS9326A, and is expected to be formed by the head-to-tail cyclodimerization of linear WS9326A and another identical peptide chain with a different acyl side chain. In vitro experiments with the N-acetylcysteamine thioesters of the corresponding monomeric intermediates and thioesterase domains of Streptomyces sp. SNM55 and S. calvus showed that this cyclodimerization reaction is directed by the substrate structures and occurs only with both linear intermediates.

Keywords: cyclodimerization; domain directed; thioesterase domain; directed substrates; cyclodimerization mohangamide; mohangamide thioesterase

Journal Title: Organic letters
Year Published: 2022

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