Convergent approaches for the synthesis of the antitumoral peptide, Kahalalide F. Study of orthogonal protecting groups.
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.
Gracia
Carolina
C
Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, 08028-Barcelona, Spain.
Isidro-Llobet
Albert
A
Cruz
Luis J
LJ
Acosta
Gerardo A
GA
Alvarez
Mercedes
M
Cuevas
Carmen
C
Giralt
Ernest
E
Albericio
Fernando
F
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
D000970:Antineoplastic Agents; D047630:Depsipeptides; C097897:kahalalide F