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Open AccessArticle

Synthesis of Lactam-Bridged and Lipidated Cyclo-Peptides as Promising Anti-Phytopathogenic Agents

1
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany
2
Center for Natural Products Research, Faculty of Chemistry, University of Havana, Zapata y G, Havana 10400, Cuba
3
Vicerrectoría de Investigación y Postgrado, Universidad Católica del Maule, Talca 3460000, Chile
*
Authors to whom correspondence should be addressed.
Academic Editors: Alexander Dömling and Shabnam Shaabani
Molecules 2020, 25(4), 811; https://doi.org/10.3390/molecules25040811 (registering DOI)
Received: 11 November 2019 / Revised: 7 February 2020 / Accepted: 7 February 2020 / Published: 13 February 2020
(This article belongs to the Special Issue Macrocycles in Drug Discovery)
Antimicrobial resistance to conventional antibiotics and the limited alternatives to combat plant-threatening pathogens are worldwide problems. Antibiotic lipopeptides exert remarkable membrane activity, which usually is not prone to fast resistance formation, and often show organism-type selectivity. Additional modes of action commonly complement the bioactivity profiles of such compounds. The present work describes a multicomponent-based methodology for the synthesis of cyclic polycationic lipopeptides with stabilized helical structures. The protocol comprises an on solid support Ugi-4-component macrocyclization in the presence of a lipidic isocyanide. Circular dichroism was employed to study the influence of both macrocyclization and lipidation on the amphiphilic helical structure in water and micellar media. First bioactivity studies against model phytopathogens demonstrated a positive effect of the lipidation on the antimicrobial activity. View Full-Text
Keywords: peptide cyclization; antimicrobial peptides (AMPs); multicomponent reactions (MCRs); lipopeptides; fungicides; antimycotics; plant pathogens peptide cyclization; antimicrobial peptides (AMPs); multicomponent reactions (MCRs); lipopeptides; fungicides; antimycotics; plant pathogens
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Vasco, A.V.; Brode, M.; Méndez, Y.; Valdés, O.; Rivera, D.G.; Wessjohann, L.A. Synthesis of Lactam-Bridged and Lipidated Cyclo-Peptides as Promising Anti-Phytopathogenic Agents. Molecules 2020, 25, 811.

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