We report not only the convergent total synthesis of falcitidin, a natural inhibitor of falcipain-2 from myxobacterium Chitinophaga, but also its diversification into a new antimalarial class of N-acyl tetrapeptides (Acyl-His-Ile-Val-Pro-NH2). Despite the lack of whole-cell activity of falcitidin itself, our study led to the identification of a trifluoromethyl (CF3) analogue displaying sub-micromolar IC50 activity against Plasmodium falciparum 3D7 in a standard blood-cell assay, but only when N-tritylated on its histidine (imidazole) residue. © 2014 Elsevier Ltd. All rights reserved.
CITATION STYLE
Kotturi, S. R., Somanadhan, B., Ch’Ng, J. H., Tan, K. S. W., Butler, M. S., & Lear, M. J. (2014). Diverted total synthesis of falcitidin acyl tetrapeptides as new antimalarial leads. Tetrahedron Letters, 55(11), 1949–1951. https://doi.org/10.1016/j.tetlet.2014.02.008
Mendeley helps you to discover research relevant for your work.