title: Convergent approaches for the synthesis of the antitumoral peptide, Kahalalide F. Study of orthogonal protecting groups.
abstract: Kahalalide compounds are peptides that are isolated from a Hawaiian herbivorous marine species of mollusc, Elysia rufescens, and its diet, the green alga Bryopsis sp. Kahalalide F and its synthetic analogues are the most promising compounds of the Kahalalide family because they show antitumoral activity. Linear solid-phase syntheses of Kahalalide F have been reported. Here we describe several new improved synthetic routes based on convergent approaches with distinct orthogonal protection schemes for the preparation of Kahaladide analogues. These strategies allow a better control and characterization of the intermediates because more reactions are performed in solution.
authors.affiliation: Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, 08028-Barcelona, Spain.
authors.forename: Carolina
authors.initials: C
authors.lastname: Gracia
authors.forename: Albert
authors.initials: A
authors.lastname: Isidro-Llobet
authors.forename: Luis J
authors.initials: LJ
authors.lastname: Cruz
authors.forename: Gerardo A
authors.initials: GA
authors.lastname: Acosta
authors.forename: Mercedes
authors.initials: M
authors.lastname: Alvarez
authors.forename: Carmen
authors.initials: C
authors.lastname: Cuevas
authors.forename: Ernest
authors.initials: E
authors.lastname: Giralt
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D008974:Mollusca / Q000378:metabolism; D011487:Protein Conformation
chemical_list: D000970:Antineoplastic Agents; D047630:Depsipeptides; C097897:kahalalide F