title: Total synthesis, structure, and oral absorption of a thiazole cyclic peptide, sanguinamide A.
abstract: The first total synthesis and three-dimensional solution structure are reported for sanguinamide A, a thiazole-containing cyclic peptide from the sea slug H. sanguineus. Solution phase fragment synthesis, solid phase fragment assembly, and solution macrocyclization were combined to give (1) in 10% yield. Spectral properties were identical for the natural product, requiring revision of its structure from (2) to (1). Intramolecular transannular hydrogen bonds help to bury polar atoms, which enables oral absorption from the gut.
authors.affiliation: Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland, Brisbane, Qld 4072, Australia.
authors.forename: Daniel S
authors.initials: DS
authors.lastname: Nielsen
authors.forename: Huy N
authors.initials: HN
authors.lastname: Hoang
authors.forename: Rink-Jan
authors.initials: RJ
authors.lastname: Lohman
authors.forename: Frederik
authors.initials: F
authors.lastname: Diness
authors.forename: David P
authors.initials: DP
authors.lastname: Fairlie
mesh_terms: D000818:Animals; D049851:Gastropoda / Q000737:chemistry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D010456:Peptides, Cyclic; D013844:Thiazoles; C579658:sanguinamide A