Organic Chemistry

Design, Synthesis and Biological Activity of 16,17-Dihydroheronamide C and ent-Heronamide C

Authors

Abstract

16,17-Dihydroheronamide C (8) and ent-heronamide C (ent-1) were designed as probes for the mode-of-action analysis of heronamide C (1). These molecules were synthesized by utilizing a highly modular strategy developed in the preceding paper. Evaluation of the antifungal activity of these compounds revealed the exceptional importance of the C16-C17 double bond for the biological activity of heronamide C, and the existence of chiral recognition between heronamide C (1) and cell membrane components.

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Content

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Supplementary material

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Supporting Information for Design, Synthesis and Biological Activity of 16,17-Dihydroheronamide C and ent-Heronamide C
MD-simulated atom distribution and tilt angle of heronamides A-C, 8-deoxyheronamide C, 16,17-dehydroheronamide C, and cholesterol in DMPC lipid bilayer; methods for the MD simulations; Raman spectra of heronamide C and 16,17-dehydroheronamide C; methods for the Raman experiments; CD spectra of 8-deoxyheronamide C, ent-heronamide C, and 16,17-dehydroheronamide C; copies of the NMR spectra of synthesized compounds (PDF)