title: Total synthesis of halicylindramide A.
abstract: A rapid and efficient Fmoc solid-phase synthesis of halicylindramide A is described. The strategy comprises resin attachment of the first amino acid via the side chain of aspartic acid, stepwise solid-phase synthesis of the linear peptide analog up to the cysteine residue, on-resin head-to-tail cyclization and linear peptide synthesis of the N-terminal region, and finally cysteine oxidation and formylation. The stereochemistry of the halicylindramide A was confirmed by comparison of NMR and RP-HPLC data with the natural molecule. A distinctive conformational change was observed from the CD spectra of the halicylindramide A in sodium dodecyl sulfate.
authors.affiliation: Department of Chemistry, Sejong University, Seoul 143-747, South Korea.
authors.forename: Hyunju
authors.initials: H
authors.lastname: Seo
authors.forename: Dongyeol
authors.initials: D
authors.lastname: Lim
mesh_terms: D002942:Circular Dichroism; D047630:Depsipeptides; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D047630:Depsipeptides; D009842:Oligopeptides; C538741:halicylindramide A