Amino-Based Probe for Natural Products with Covalent Binding Ability to Lysine and Mechanism of Action of Medermycin
A chemoselective amino-based probe was designed for discovering natural products with covalent binding potential to lysine. Using this reactivity-based technique, a marine-derived <i>Streptomyces</i> strain was identified, which could produce medermycin as the major metabolite. A new compound, mederpyrrole A, derived from medermycin and anthranilic acid through nonenzymatic reaction was isolated. Medermycin can react with primary amines under mild conditions to generate chimeric products possessing a naphthoquinone-pyrrole skeleton. It can also covalently bind to proteins.
Authors
- Shupeng Yin (ORCID: https://orcid.org/0000-0002-8571-8075)
- Jingjing Shen (ORCID: https://orcid.org/0000-0001-5754-4066)
- Weiming Zhu (ORCID: https://orcid.org/0000-0002-7591-3264)
- Peng Fei Fu (ORCID: https://orcid.org/0000-0002-7768-4004)
- Chao Gao (ORCID: https://orcid.org/0000-0002-5205-0670)
- Weihong Wang (ORCID: https://orcid.org/0000-0002-7022-3897)
- Jiaxu Shang
- Ke Sun (ORCID: https://orcid.org/0000-0002-3789-3143)
Institutions
- Qingdao National Laboratory for Marine Science and Technology (CN)
- Ocean University of China (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-19
- DOI
- https://doi.org/10.1021/acs.orglett.4c03803
- Citations
- 3
- Primary Topic
- Microbial Natural Products and Biosynthesis
- Type
- article
- Field-Weighted Citation Impact
- 1.34
Funders
- National Natural Science Foundation of China
- Taishan Scholar Project of Shandong Province