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Structure Revision and the Biosynthetic Pathway of Tripartilactam
- Title
- Structure Revision and the Biosynthetic Pathway of Tripartilactam
- Authors
- Hwang, Sunghoon; Kim, Eunji; Lee, Jeeyeon; Shin, Jongheon; Yoon, Yeo Joon; Oh, Dong-Chan
- Ewha Authors
- 윤여준
- SCOPUS Author ID
- 윤여준
- Issue Date
- 2020
- Journal Title
- JOURNAL OF NATURAL PRODUCTS
- ISSN
- 0163-3864
1520-6025
- Citation
- JOURNAL OF NATURAL PRODUCTS vol. 83, no. 3, pp. 578 - 583
- Publisher
- AMER CHEMICAL SOC
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- Tripartilactam (1) is a natural macrocyclic lactam originally reported to have a unique [18,8,4]-tricyclic framework. However, the validity of this structure has been contested since niizalactam C (2), bearing a [18,6,6]-tricyclic skeleton, was proposed as an alternative structure in 2015. In the present study, a comprehensive reinvestigation of NMR spectroscopic data and a C-13-C-13 COSY NMR experiment identified direct C-13-C-13 coupling, thus leading to the unequivocal revision of the structure of tripartilactam as niizalactam C (2). In addition, whole-genome sequencing analysis of the tripartilactam-producing bacterial strain and subsequent bioinformatics and mutagenesis analyses identified its biosynthetic pathway, which probably utilizes one of the type I polyketide synthase (PKS) modules iteratively during its biosynthesis and exhibits spontaneous [4+2] cycloaddition from the precursor compound, sceliphrolactam, in the post-PKS process.
- DOI
- 10.1021/acs.jnatprod.9b00819
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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