Total Synthesis, Structure Elucidation, and Bioactivity Evaluation of the Cyclic Lipopeptide Natural Product Paenilipoheptin A
In this study, we further investigated the structure of the recently reported cyclic lipopeptide natural product paenilipoheptin A. Here, we disclose the first total synthesis of the compound, allowing for its complete structural assignment. The route developed employs automated SPPS, providing access to the compound in quantities suitable for antibacterial and antifungal testing. These studies unequivocally establish the stereochemical framework of paenilipoheptin A and further reveal that the compound possesses moderate activity against Gram-positive bacteria.
Authors
- Nataliia V. Machushynets (ORCID: https://orcid.org/0000-0002-8530-1966)
- Jisca L. van Dam (ORCID: https://orcid.org/0000-0002-7564-4711)
- Alexander Speer (ORCID: https://orcid.org/0000-0001-7142-5987)
- Arthur F. J. Ram (ORCID: https://orcid.org/0000-0002-2487-8016)
- Cornelis J. Slingerland (ORCID: https://orcid.org/0000-0003-0027-7491)
- Nathaniel I. Martin (ORCID: https://orcid.org/0000-0001-8246-3006)
- Gilles P. van Wezel (ORCID: https://orcid.org/0000-0003-0341-1561)
- Vladyslav Lysenko (ORCID: https://orcid.org/0000-0001-9236-5821)
- Fabienne A. C. Sterk
Institutions
- Leiden University (NL)
- Netherlands Institute of Ecology (NL)
- Amsterdam University Medical Centers (NL)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-18
- DOI
- https://doi.org/10.1021/acs.orglett.5c00232
- Citations
- 7
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 6.55
Funders
- Nederlandse Organisatie voor Wetenschappelijk Onderzoek