title: The amido-pentadienoate-functionality of the rakicidins is a thiol reactive electrophile--development of a general synthetic strategy.
abstract: We demonstrate that a unique class-defining functionality (mc-APD) found in macrocyclic natural products with potent anti-cancer activity, imparts these compounds with electrophilic reactivity. The mc-APD group represents an interesting structural hybrid between canonical biologically relevant Michael-acceptors. Further, a novel thiol-elimination method for preparation of the mc-APD group is outlined.
authors.affiliation: Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark. thpou@chem.au.dk.
authors.forename: Lise L
authors.initials: LL
authors.lastname: Clement
authors.forename: Michail
authors.initials: M
authors.lastname: Tsakos
authors.forename: Eva S
authors.initials: ES
authors.lastname: Schaffert
authors.forename: Carsten
authors.initials: C
authors.lastname: Scavenius
authors.forename: Jan J
authors.initials: JJ
authors.lastname: Enghild
authors.forename: Thomas B
authors.initials: TB
authors.lastname: Poulsen
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry*; D055666:Lipopeptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry*; D012710:Serum Albumin, Bovine / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D047630:Depsipeptides
chemical_list: D000970:Antineoplastic Agents; D055666:Lipopeptides; D010456:Peptides, Cyclic; D012710:Serum Albumin, Bovine; D013438:Sulfhydryl Compounds; C000723972:rakicidins; D047630:Depsipeptides