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. 2023 Nov 15:96:129506.
doi: 10.1016/j.bmcl.2023.129506. Epub 2023 Oct 12.

Total and chemoenzymatic synthesis of the lipodepsipeptide rhizomide A

Corinne A Lepetit  1 , André R Paquette  2 , Jordan T Brazeau-Henrie  2 , Christopher N Boddy  3
Affiliations

Total and chemoenzymatic synthesis of the lipodepsipeptide rhizomide A

Corinne A Lepetit et al. Bioorg Med Chem Lett. .

Abstract

Rhizomides are a family of depsipeptide macrolactones synthesized by a non-ribosomal peptide synthetase (NRPS) encoded in the genome of Paraburkholderia rhizoxinica str. HKI 454. In this study, the total and chemoenzymatic synthesis of the depsipeptide rhizomide A is described. Rhizomide A was generated through macrolactamization while thelinear C-terminal N-acetylcysteamine (SNAC) thioester substrate was synthesized through a C-terminal thioesterification strategy. It was shown that the rhizomide A thioesterase (RzmA-TE) is an active macrocyclization catalyst, allowing the chemoenzymatic synthesis of rhizomide A.This work further showcases the biocatalytic power of TEs in accessing complex macrocyclic natural products.

Keywords: Biocatalysis; Chemoenzymatic synthesis; Depsipeptide; Enzymatic assays; Peptide chemistry; Total synthesis.

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Conflict of interest statement

Declaration of Competing Interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Christopher N. Boddy reports financial support was provided by Natural Sciences and Engineering Research Council of Canada.

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