Modular Solid-Phase Synthesis of Antiprotozoal Barnesin Derivatives.
(2020) Modular Solid-Phase Synthesis of Antiprotozoal Barnesin Derivatives. Org Lett , PubMed
ILRS Authors
Luka Raguz Francois Keiff David Roman
Projects
Modular synthetic approaches towards natural sphingoid base-type signaling molecules
Details
Organic synthetic method development and total synthesis of microbial derived natural products
Details
Synthesis of bio-active molecules and their derivatives, and Evaluation of their bio-activities
Details
Abstract
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.
Identifier
doi: 10.1021/acs.orglett.0c00723 PMID: 32212714
