Total and chemoenzymatic synthesis of the lipodepsipeptide rhizomide A

被引：5

作者：

Lepetit, Corinne A. ^{[1
,2
]}

Paquette, Andre R. ^{[1
]}

Brazeau-Henrie, Jordan T. ^{[1
]}

Boddy, Christopher N. ^{[1
]}

机构：

[1] Univ Ottawa, Ctr Chem & Synthet Biol, Dept Chem & Biomol Sci, Ottawa, ON K1N 6N5, Canada

[2] Cergy Paris Univ, 5 Mail Gay Lussac, F-95000 Cergy, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2023年 / 96卷

关键词：

Depsipeptide; Chemoenzymatic synthesis; Total synthesis; Biocatalysis; Peptide chemistry; Enzymatic assays; THIOESTERASE DOMAIN; PEPTIDE; CYCLIZATION; CYCLASE;

D O I：

10.1016/j.bmcl.2023.129506

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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 the linear 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.

引用

页数：5

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