title: Total solid-phase synthesis of marine cyclodepsipeptide IB-01212.
abstract: A suitable combination of synthetic design, orthogonal protecting groups and coupling reagents was used to complete the first known synthesis of the natural marine cyclodepsipeptide IB-01212. The cyclic, symmetric octapeptide contains two of each of the following residues: L-N,N-Me2Leu, L-Ser, L-N-MeLeu and L-N-MePhe. IB-01212 also features two symmetric ester bonds between the hydroxyl group of Ser and the carboxyl function of the N-MePhe. Total solid-phase syntheses of the product was performed in parallel via three distinct routes: dimerization of heterodetic fragments, linear synthesis, and convergent synthesis. The convergent strategy gave the best results in terms of product yield and purity and is particularly suitable for the large-scale synthesis of IB-01212 and similar peptides.
authors.affiliation: Barcelona Biomedical Research Institute, Barcelona Science Park, University of Barcelona, 08028-Barcelona, Spain.
authors.forename: Luis J
authors.initials: LJ
authors.lastname: Cruz
authors.forename: Carmen
authors.initials: C
authors.lastname: Cuevas
authors.forename: Librada M
authors.initials: LM
authors.lastname: Cañedo
authors.forename: Ernest
authors.initials: E
authors.lastname: Giralt
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D019281:Dimerization
chemical_list: D000903:Antibiotics, Antineoplastic; D047630:Depsipeptides; C519452:IB-01212