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Discovery and Biosynthesis of Cihunamides, Macrocyclic Antibacterial RiPPs with a Unique C−N Linkage Formed by CYP450 Catalysis
- Title
- Discovery and Biosynthesis of Cihunamides, Macrocyclic Antibacterial RiPPs with a Unique C−N Linkage Formed by CYP450 Catalysis
- Authors
- An J.S.; Lee H.; Kim H.; Woo S.; Nam H.; Lee J.; Lee J.Y.; Nam S.-J.; Lee S.K.; Oh K.-B.; Kim S.; Oh D.-C.
- Ewha Authors
- 남상집
- SCOPUS Author ID
- 남상집
- Issue Date
- 2023
- Journal Title
- Angewandte Chemie - International Edition
- ISSN
- 1433-7851
- Citation
- Angewandte Chemie - International Edition vol. 62, no. 26
- Keywords
- Antibacterial Natural Products; Biosynthesis; Cytochrome P450 Enzymes; RIPPs; Structural Elucidation
- Publisher
- John Wiley and Sons Inc
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- Cihunamides A–D (1–4), novel antibacterial RiPPs, were isolated from volcanic-island-derived Streptomyces sp. The structures of 1–4 were elucidated by 1H, 13C, and 15N NMR, MS, and chemical derivatization; they contain a tetrapeptide core composed of WNIW, cyclized by a unique C−N linkage between two Trp units. Genome mining of the producer strain revealed two biosynthetic genes encoding a cytochrome P450 enzyme and a precursor peptide. Heterologous co-expression of the core genes demonstrated the biosynthesis of cihunamides through P450-mediated oxidative Trp-Trp cross-linking. Further bioinformatic analysis uncovered 252 homologous gene clusters, including that of tryptorubins, which possess a distinct Trp-Trp linkage. Cihunamides do not display the non-canonical atropisomerism shown in tryptorubins, which are the founding members of the “atropitide” family. Therefore, we propose to use a new RiPP family name, “bitryptides”, for cihunamides, tryptorubins, and their congeners, wherein the Trp-Trp linkages define the structural class rather than non-canonical atropisomerism. © 2023 Wiley-VCH GmbH.
- DOI
- 10.1002/anie.202300998
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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