Total synthesis of halicylindramide A.
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.
Seo
Hyunju
H
Department of Chemistry, Sejong University, Seoul 143-747, South Korea.
Lim
Dongyeol
D
D002942:Circular Dichroism; D047630:Depsipeptides; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D047630:Depsipeptides; D009842:Oligopeptides; C538741:halicylindramide A