Total synthesis of Crotogossamide using an on-resin concomitant cyclization/cleavage reaction. (August 2018)

• Record Type: Journal Article
• Authors: Bérubé, Christopher; Borgia, Alexandre; Simon, Gaëlle; Grenier, Daniel; Voyer, Normand
• Is Part Of: Phytochemistry letters. Volume 26(2018)
• Page Start: 101
• Page End: 105
• Publication Date: 2018-08
• Subjects: Crotogossamide -- Cyclic peptides -- Macrocycles -- Oxime resin -- Peptide synthesis; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2018.05.021
• Languages: English
• ISSNs: 1874-3900

Abstract

Graphical abstract: Highlights: Expedient Crotogossamide synthesis by on-resin concomitant cyclization/cleavage. Antibacterial and anti-biofilm activity of Crotogossamide were investigated. Efficient synthetic strategy towards cyclic peptide phytochemicals using oxime resin. Abstract: Crotogossamide, a cyclic peptide isolated from the latex of Croton gossypifolius, has been synthesized by a rapid and efficient Boc solid-phase peptide synthesis. The strategy takes advantage of the oxime resin nucleophile susceptibility and comprises the synthesis of a linear precursor followed by on-resin head-to-tail concomitant cyclization/cleavage. In addition, we report the first antimicrobial and antibiofilm investigations on Crotogossamide.