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.
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页数：5
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