Journal
ORGANIC LETTERS
Volume 22, Issue 10, Pages 3744-3748Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00723
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Funding
- German Research Foundation (DFG) [BE 4799/2-1]
- ERC [802736 MORPHEUS]
- Infect Control 2020 [FKZ 03ZZ0803A, FKZ 03ZZ0826A, FKZ 03ZZ0835A]
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Here, we applied and optimized a solid support (SP)-based Horner-Wadsworth-Emmons reagent to prepare SP-bound vinylogous amino acids. Subsequent SP-based peptide synthesis, global deprotection, and chemical modifications yielded 14 lipodipeptides carrying vinylogous amino acids, including the natural product barnesin A (1). Biological evaluation revealed that several synthesized derivatives show micromolar to nanomolar inhibitory activity against papain-like cysteine proteases, human cathepsin L, and rhodesain.
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